1-norbornan-2-yl propan-2-one as a fragrance

Abstract

Use of 1-norbornan-2-ylpropan-2-one as a fragrance is presented.

Description

TECHNICAL FIELD

[0001] The present invention relates to the use of 1-norbornan-2-ylpropan-2-one as a fragrance. Furthermore, the present invention relates to fragrance compositions, their use and methods for imparting, modifying and / or enhancing certain fragrance notes. BACKGROUND

[0002] In terms of the perfume industry, there is always a need for new perfume creations. However, the creation of new fragrances or fragrance compositions involves many challenges. For example, it is necessary to select a specific composition of several fragrances from the almost infinite number of possible structures known from the prior art in order to meet the specific needs of the market and to provide a product that matches the specific characteristics desired by the customer. Suitable fragrances exhibit very beneficial properties, but in combination with other fragrances can produce unpleasant and thus detrimental odors, making them difficult or even impossible to use for a specific purpose.

[0003] A second important issue relates to the need to provide fragrance compositions that not only conform to a specific odor profile but also have so-called secondary beneficial properties. In fact, many fragrance compositions known on the market have significant drawbacks in use, such as poor solubility and storage stability, but also deficiencies in subjective issues such as tenor, charisma, etc. Furthermore, many known fragrance compositions require high dosages to achieve the desired odor result. A further requirement for fragrances at present is high biodegradability as well as dermatological and toxicological safety. Therefore, there is a particularly high need to provide a fragrance that has a great impact on other fragrances even at small dosages and that transforms a rather unpleasant odor impression into a positive odor impression and / or enhances a pleasant odor impression.

[0004] Thus, the underlying problem of the present invention is to provide a new fragrance that is able to enhance the positive and beneficial odor aspects of other fragrances and / or (at the same time) reduce, inhibit and / or mask undesirable unpleasant odor aspects. In particular, the new fragrance should also have the feature of improving the stability, solubility and overall performance of other fragrances, as well as reducing the required dosage. Finally, the fragrance composition itself should have excellent biodegradability and be harmless to humans and the environment. SUMMARY

[0005] This is solved by using 1-norbornan-2-ylpropan-2-one as a fragrance.

[0006] The 1-norbornan-2-ylpropan-2-one used according to the present invention can be present in any stereoisomeric form or can be present in any mixture of stereoisomers.

[0007] What is described for 1 -norbornan-2-ylpropan-2-one, in particular the described advantages, also applies to the mixtures of stereoisomers of 1 -norbornan-2-ylpropan-2-one used according to the application.

[0008] 1 -norbornan-2-ylpropan-2-one has very unique olfactory properties, which clearly distinguish it from and also exceed the olfactory properties of known odorants. The suitability of 1 -norbornan-2-ylpropan-2-one as a fragrance was previously unknown. It is therefore particularly surprising that in a field that has been thoroughly researched, a fragrance with valuable, interesting and complex olfactory properties can be found.

[0009] 1 -norbornan-2-ylpropan-2-one has the following structural formula

[0010]

[0011] and, preferably, the following characteristics: Cas number: 31683-73-5.

[0012] As mentioned above, its suitability as a fragrance was previously unknown. Equally, there is no precise odor description, however, according to the present inventors, 1 -norbornan-2-ylpropan-2-one smells fruity, close to isoamyl acetate and wintergreen.

[0013] The present inventors have therefore surprisingly found that 1 -norbornan-2-ylpropan-2-one is suitable as a fragrance and, in small doses, in combination with odorant compounds that are different from 1 -norbornan-2-ylpropan-2-one, produces a special effect.

[0014] In a preferred embodiment according to the application, 1 -norbornan-2-ylpropan-2-one is used to enhance one or more pleasant olfactory impressions of one or more odorant compounds, wherein the compound / compounds are different from 1 -norbornan-2-ylpropan-2-one. Preferably, the one or more pleasant olfactory impressions of the one or more odorant compounds are selected from the group consisting of the enhancement and / or improvement of the floral and / or naturalness - in particular a more lavender-like odor. This means that 1 -norbornan-2-ylpropan-2-one preferably enhances or improves the floral and / or naturalness of odorant compounds. In particular, 1 -norbornan-2-ylpropan-2-one makes the olfactory impression of these substances more lavender-like.

[0015] As used herein, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. For example, the term "a compound" or "at least one compound" can include more than one compound, including mixtures thereof. In addition, the plural form includes singular embodiments unless the context clearly dictates otherwise. For example, the term "one or more odorant compounds" also includes embodiments having only one odorant compound.

[0016] In fact, the 1 -norbornan-2-yl propan-2-ones used according to the present application can impart a very complex and varied overall sensory impression, which is usually only achieved by mixtures of several components, such as essential oil or perfume mixtures, and is therefore particularly surprising.

[0017] In addition to the primary, i.e. olfactory properties, the 1 -norbornan-2-yl propan-2-ones also have positive secondary properties, in particular a high substantivity compared to perfumes with similar olfactory properties, as well as a high stability in certain media and formulations, a high extensibility, and are also biodegradable.

[0018] It is also recognized that the 1 -norbornan-2-yl propan-2-ones can function excellently as so-called boosters (amplifiers; enhancers). Preferably, the 1 -norbornan-2-yl propan-2-ones are used as boosters of one or more pleasant olfactory impressions of one or more odorant compounds. In other words: the 1 -norbornan-2-yl propan-2-ones, when used together with other odorant compounds, enhance the pleasant odor note thereof.

[0019] Furthermore, the 1 -norbornan-2-yl propan-2-ones used according to the present application can enhance the strength of a perfume composition and round the overall odor of a mixture. Thus, the compounds described herein can be used to impart more floral and / or naturalness to other compounds, in particular odorant compounds having at least one or more pleasant olfactory impressions. In addition, the 1 -norbornan-2-yl propan-2-ones are suitable as agents for increasing the substantivity and / or retention of a perfume composition.

[0020] In the context of the present application, "odorant compounds" are generally understood to be substances which elicit one or more pleasant odor impressions, whether as primary or as secondary / subordinate olfactory notes. The terms "odorant compounds" and "perfume" are used interchangeably in the context of the present application.

[0021] Preferably, the one, more or all odorant compounds different from 1 -norbornan-2- ylpropan-2-one are selected from the group comprising fragrances having a molar mass in the range of 150 g / mol to 285 g / mol, in particular alcohols, aldehydes, ketones, ethers, esters and carboxylate salts having a molar mass in the range of 150 g / mol to 285 g / mol.

[0022] More preferably, the one, more or all odorant compounds are selected from the group comprising 4-methoxybenzaldehyde, borneol, isoborneol, 1 -benzopyran-2-one, 2-ethyl-3- hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7- dimethyl-2,7-octadien-1 -ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenoate, camphoran-2-on, lavandin, 3,7- dimethylocta-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1 -ol, (2Z)-3,7-dimethylocta- 2,6-dien-1 -ol, nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7- dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1 -(propan-2- yl)cyclohex-3-en-1 -ol, p-menth-1 -ene-8-ol, 2-(4-methylcyclohex-3-en-1 -yl)propan-2-ol, 4- hydroxy-3-methoxybenzaldehyde.

[0023] In a preferred embodiment according to the application, the ratio of the total mass of odorant compounds to the total mass of (methoxymethyl)-2-methylbenzene is in the range of 1 to 1000 to 1 to 100, preferably 1 to 600 to 1 to 400.

[0024] 1 -norbornan-2-ylpropan-2-one can be used in a variety of products; it can be used as a single fragrance, but it can particularly advantageously be combined with other odorant compounds, in particular fragrances, in different ratios to form a fragrance mixture and can also result in novel and original fragrance compositions.

[0025] An aspect of the present application therefore also relates to a fragrance mixture and possibly other ingredients (solvents, etc.) containing 1 -norbornan-2-ylpropan-2-one.

[0026] The perfume composition according to the present application comprises or consists of 1- norbornan-2-ylpropan-2-one and at least one further odoriferous compound different from 1-norbornan-2-ylpropan-2-one. Preferably, the perfume composition according to the present application comprises or consists of 1-norbornan-2-ylpropan-2-one and two or more further odoriferous compounds different from 1-norbornan-2-ylpropan-2-one. More preferably, the perfume composition according to the present application comprises or consists of 1-norbornan-2-ylpropan-2-one and three or more odoriferous compounds different from 1-norbornan-2-ylpropan-2-one. Most preferably, the perfume composition according to the present application comprises or consists of 1-norbornan-2-ylpropan-2-one and four or more further odoriferous compounds different from 1-norbornan-2-ylpropan-2-one.

[0027] The 1-norbornan-2-ylpropan-2-one according to the present application is typically used in a sensorially effective amount, i.e. in a total amount in which it exerts a sensorial effect.

[0028] Preferably, the weight ratio of 1-norbornan-2-ylpropan-2-one to the total amount of odoriferous compounds different from 1-norbornan-2-ylpropan-2-one is in the range of 1 to 1000 to 1 to 100, preferably 1 to 600 to 1 to 400.

[0029] In a preferred embodiment according to the present application, 1-norbornan-2-ylpropan-2-one is comprised in the perfume composition in a sensorially effective amount sufficient to enhance one or more pleasant olfactory impressions of one or more odoriferous compounds different from 1-norbornan-2-ylpropan-2-one, in particular to enhance or improve the floral and / or naturalness of one or more odoriferous compounds, in particular more lavender-like.

[0030] Examples of odoriferous compounds, in particular perfumes, which can be advantageously combined with 1-norbornan-2-ylpropan-2-one in the context of the present application are found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N.J. 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0031] In particular mentioned are: extracts from natural raw materials, such as essential oils, concretes, absolutes, resins, balsams, oleoresins, tinctures, for example:

[0032] Ambergris tincture, Amyris oil, Angelica seed oil, Angelica root oil, Anise oil, Valerian oil, Basil oil, Blumea oil absolute, Laurel leaf oil, Wormwood oil, Benzoin resin, Bergamot oil, Beeswax absolute, Birch tar oil, Bitter Almond oil, Savory oil, Buchu leaf oil, Brazilian Rosewood oil, Juniper berry oil, Calamus oil, Camphor oil, Ylang-ylang oil, Cardamom oil, Caraway oil, Cassia oil, Cassie absolute, Castoreum absolute, Cedar leaf oil, Cedarwood oil, Cistus oil, Citronella oil, Lemon oil, Copaiba balsam, Copaiba balsam oil, Coriander oil, Costus root oil, Cumin oil, Cypress oil, Davana oil, Eau de brouts-Absolue, Evergreen fir needle oil, Galbanum oil, Tarragon oil, Tarragon seed oil, Eucalyptus citriodora oil, Eucalyptus oil, Fennel oil, Fir needle oil, Galbanum oil, Galbanum resin, Geranium oil, Grapefruit oil, Guaiacwood oil, Gurjun balsam, Gurjun balsam oil, Heliotrope absolute, Heliotrope oil, Ginger oil, Iris root absolute, Iris root oil, Jasmine absolute, White Flag lily oil, Blue Cornflower oil, Roman Chamomile oil, Carrot seed oil, Cassie oil, Pine needle oil, Peppermint oil, Caraway oil, Cistus oil, Cistus absolute, Cistus resin, Lavandin absolute, Lavandin oil, Lavender absolute, Lavender oil, Lemon grass oil, Lovage oil, Distilled White Lemon oil, Pressed White Lemon oil, Linaloe oil, Litsea cubeba oil, Laurel leaf oil, Nutmeg oil, Marjoram oil, Mandarin oil, Massoir bark oil, Mimosa absolute, Mucuna seed oil, Mucuna tincture, Mugwort oil, Nutmeg oil, Oud absolute, Oud oil, Myrtle oil, Clove leaf oil, Clove flower oil, Neroli oil, Oud absolute, Oud oil, Rue oil, Rosemary oil, Dalmatian Sage oil, Spanish Sage oil, Sandalwood oil, Sesame seed oil, Spike lavender oil, Star anise oil, Styrax oil, Tagetes oil, Tea tree oil, Turpentine oil, Thyme oil, Tolu balsam, Tonka absolute, Tuberose absolute, Vanilla extract, Violet leaf absolute, Verbena oil, Vetyver oil, Juniper oil, Grape seed oil, Wormwood oil, Wintergreen oil, Ylang-ylang oil, Yarrow oil, Civet absolute, Cinnamon leaf oil, Cinnamon bark oil, and fractions thereof or contents isolated therefrom;

[0033] Individual flavoring agents selected from hydrocarbons such as 3-carene, alpha-pinene, beta-pinene, alpha-terpinene, gamma-terpinene, p-cymene, benzyl alcohol, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;

[0034] Fatty 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;

[0035] Fatty aldehydes and their acyals 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 acyl, 1,1 -dimethoxy-2,2,5-trimethyl-4-hexene, citronellyloxyacetaldehyde, 1 -(1 -methoxy-propoxy)-(E / Z)-3-hexene;

[0036] Fatty 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, 6-methyl-5-hepten-2-one;

[0037] Fatty sulfur-containing compounds such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetythiohexyl acetate, 1 -menthene-8-thiol;

[0038] Fatty nitriles such as 2-nonenitrile, 2-undecenenitrile, 2-tridecenenitrile, 3,12-tridecadienoic acid, 3,7-dimethyl-2,6-octadienenitrile, 3,7-dimethyl-6-octenenitrile;

[0039] Aliphatic carboxylic acid esters such as formic acid (E) and (Z)-3-hexenyl ester, ethyl acetoacetate, isoamyl acetate, 3,5,5-trimethyl-hexyl 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, hexyl crotonate, ethyl isovalerate, ethyl 2-methylvalerate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, allyl heptanoate, ethyl octanoate, ethyl (E,Z)-2,4-decadienoate, methyl 2-octenoate, methyl 2-nonenate, allyl 2- isopentyloxyacetate, methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

[0040] Non-cyclic terpene alcohols such as geraniol, nerol, Lavadulol, nerolidol, farnesol, tetrahydrolinalool, tetrahydrogeraniol; 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; 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-dimethyloct-6- en-1-ol, (2E)-3,7-dimethylocta-2,6-dien-1-ol, 3,7-dimethyl-1,5,7-octatrien-3-ol, 2,6-dimethyl-2,5,7- octatrien-1-ol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, Tiglinates and 3-methyl-2-butenates;

[0041] Non-cyclic terpene aldehydes and ketones such as citronellal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranylacetone, and dimethyl and diethyl acetal of citral and neral;

[0042] Cyclic terpene alcohols such as menthol, isopulegol, alpha-terpineol, terpineol-4, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambratal, vetiverol, guaiol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, Tiglinates, 3-methyl-2-butenates;

[0043] Cyclic terpene aldehydes and ketones, such as menthone, isomenthone, 8-mercapto menthan-3-one, carvone, camphor, fenchone, a-ionone, β-ionone, a-n-methylionone, β-n-methylionone; a-isomethylionone, β-isomethylionone, a-irone, 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-methanona- phthalene-8(5H)-one, 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal, nuciferone, dihydronuciferone, 4,6,8-megastigmatrien-3-one, a-sinensal, β-sinensal, acetylcedrene (methyl cedryl ketone); cyclic alcohols, such as, for example: 4-tert.-butylcyclohexanol, 3,3,5-trimethyl-cyclohexanol, 3-isocamphylcyclohexanol, 2,6,9-trimethyl-(Z2,Z5,E9)-cyclododecatrien-1 -ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol; 4-cyclohexylbutan-2-ol;

[0044] Cyclic aliphatic alcohols, such as a-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)-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-trimethylcyclohexyl)hexan-3-ol;

[0045] Cyclic ethers and cyclic aliphatic ethers, for example: eucalyptol, methyl cedryl ether, cyclododecyl methyl ether, 1,1 -dimethoxycyclododecane, (ethoxymethoxy)cyclododecane, a-cedrene oxide, 3a,6,6,9a-tetramethyldodecahydronaphthalenol[2,1 -b]furan, 3a-ethyl-6,6,9a-trimethyldodecahydronaphthalenol[2,1 -b]furan, 1,5,9-trimethyl-13-oxabicyclo[10.1.0]-tridec-4,8-diene, rose oxide, 2-(2,4-dimethyl-3-cyclohexen-1 -yl)-5-methyl-5-(1 -methylpropyl)-1,3-dioxane;

[0046] Cyclic ketones and macrocyclic ketones, such as: 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-cyclopentadecanone, 3-methylcyclopentadecanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 4-tert-amylcyclohexanone, 5-cyclohexadecene-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 8-cyclohexadecene-1-one, 9-cycloheptadecene-1-one, cyclopentadecanone, cyclohexadecenecanone;

[0047] Cyclic aldehydes, such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenal, and 4-(4-methyl-3-penten-1-yl)-3-cyclohexenal;

[0048] Cyclic 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-naphthylmethyl ketone, methyl-2,6,10-trimethyl-2,5,9-cyclododecanetrienone, tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl)one;

[0049] Esters of cycloalcohols, such as 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-cyclopentyl cyclopentylcrotonate, 3-pentyl-tetrahydro-2H-pyran-4 ester of acetate, and decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate. Acetic acid 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indanate, propionic acid 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indanate, isobutyric acid 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indanate, acetic acid 4,7-formyloxy-octahydro-5- or -6-indanate,

[0050] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

[0051] Cycloaliphatic carboxylic acid esters, such as allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis- and trans-dihydrojasmone methyl ester, cis- and trans-jasmone methyl ester, methyl 2-hexyl-3-oxocyclopentene carboxylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexene carboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexene carboxylate, ethyl 2-methyl-1,3-dioxolane-2-acetate;

[0052] Aryaliphatic alcohols, such as benzyl alcohol, 2-phenylethanol, 1-phenylethanol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethanol, 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;

[0053] Esters of arylaliphatic 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, alpha-trichloromethyl benzyl acetate, ethyl alpha,alpha-dimethylphenyl acetate, ethyl alpha,alpha-dimethylphenyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, 4-methoxybenzyl acetate;

[0054] Aryaliphatic ethers, such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl-1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno-[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno-[1,2-d]-m-dioxine;

[0055] aromatic and araliphatic aldehydes, such as, for example: benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, Hydratropaaldehyd, 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-butylphenyl)propanal, cinnamaldehyde, α-butylcinnamaldehyde, α-hexylcinnamaldehyde, 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; aromatic and araliphatic ketones, such as acetophenone, 4-methyl-acetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthyl)ethanone, 2-benzofuranethanone, 3-methyl-2-benzofuranyl)ethanone, benzophenone, 1,1,2,3,6-hexamethyl-5-indanylmethyl ketone, 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-ethylnaphthalenone;

[0056] aromatic and araliphatic carboxylic acids and their esters, such as benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenylacetate, ethyl phenylacetate, geranyl phenylacetate, phenyl phenylacetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenyl cinnamate; cinnamyl cinnamate, allyl phenoxyacetate, methyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate;

[0057] 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;

[0058] Lactones, such as 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, 9-hexadecen-1,16-olide, 10-oxo-1,16-hexadecanolide, 11-oxo-1,16-hexadecanolide, 12-oxo-1,16-hexadecanolide, vinyl-1,12-dodecanedio-lide, vinyl-1,13-tridecanedio-lide, 2,3-dihydrocoumarin, octahydrocoumarin.

[0059] In another preferred embodiment of the present application, 1 -norbornan-2-yl propan-2-one is preferably combined with one or more, particularly preferably two, three, four, five or more odorant compounds.

[0060] The 1 -norbornan-2-yl propan-2-one used according to the application advantageously (at least partially) achieves an olfactory enhancement of the pleasant olfactory impression.

[0061] Preferably, the one, more or all odorant compounds different from 1 -norbornan-2-yl propan-2-one are selected from the group comprising fragrances having a molar mass in the range from 150 g / mol to 285 g / mol, in particular alcohols, aldehydes, ketones, ethers, esters and carboxylic acid salts having a molar mass in the range from 150 g / mol to 285 g / mol.

[0062] In another preferred embodiment according to the application, the one, more or all odorant compounds are selected from the group comprising 4-methoxybenzaldehyde, borneol, isoborneol, 1-benzopyran-2-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7-dimethyl-2,7- octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenoate, camphoran-2-on, lavandin, 3,7-dimethylocta-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1 -ol, (2Z)-3,7-dimethylocta-2,6-dien-1-ol, nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7-dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol, p-menth-1 -ene-8-ol, 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol, 4-hydroxy-3-methoxybenzaldehyde.

[0063] Preferably, 1 -norbornan-2-yl propan-2-one is combined with one or more, particularly preferably with two, three, four, five or more of those preferred odorant compounds.

[0064] The fragrance oil composition containing 4-cyclohexyl-2-butanol is advantageously used for perfuming in liquid form, undiluted or diluted with a solvent. Suitable solvents for this purpose are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butanediol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and the like.

[0065] Furthermore, the fragrance composition according to the application can be adsorbed on a carrier, which ensures both a fine distribution of the fragrance in the product and a controlled release during use. This carrier can be a porous inorganic material, such as light sulphate, silica gel, zeolite, gypsum, clay, clay granules, aerated concrete and the like, or an organic material, such as wood, cellulose-based substances, sugar, dextrin (e.g. maltodextrin) or plastics, such as PVC, polyvinyl acetate or polyurethane. The final combination of the composition according to the application and the carrier substance is also to be understood as a fragrance composition according to the application.

[0066] The perfume composition according to the application can also be microencapsulated, spray-dried, as a clathrate or as an extruded product and added in this form to the product to be perfumed.

[0067] If desired, the properties of the composition modified in this way can be further optimized by a so-called "coating" with a suitable material in order to release the perfume more targeted, for which it is preferred to use a waxy plastic, such as polyvinyl alcohol. The resulting product in turn represents an article according to the application.

[0068] Preferably, the amount of 1-norbornan-2-yl propan-2-one is from 0.01 to 50% by weight, based on the total weight of the perfume composition. More preferably, the amount of 1-norbornan-2-yl propan-2-one is from 0.01 to 10% by weight, based on the total weight of the perfume composition. More preferably, the amount of 1-norbornan-2-yl propan-2-one is from 0.1 to 2.5% by weight, based on the total weight of the perfume composition.

[0069] The perfume composition according to the application can advantageously be used in concentrated form, in solution form or in the modified forms mentioned above for the production of perfumed articles according to the application, such as perfume extracts, eau de parfum, eau de toilette, shaving lotions, colognes, pre-shave products, splash colognes and perfumed wet wipes, perfuming for acidic, basic and neutral cleaners, such as floor cleaners, glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring pastes, solid and liquid toilet cleaners, carpet cleaners in powder and foam form, textile fresheners, ironing aids, liquid laundry compositions, powdery laundry compositions, laundry pretreatments such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, laundry tablets, disinfectants, air fresheners in liquid form, gel type or applied to solid support form, aerosol sprays, waxes and polishes, such as furniture polishes, floor waxes, shoe creams and personal care products, such as solid and liquid soaps, shower and bath gels, shampoos, shaving soaps, shaving foams, bath oils, emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water type, such as skin creams and emulsions, face creams and emulsions, sunscreens and emulsions, after-sun lotions and emulsions, hand creams and emulsions, foot creams and emulsions, depilatory creams and emulsions, aftershave creams and emulsions, tanning creams and emulsions, hair care products, such as hair sprays, hair gels, hair fixatives, hair conditioners, permanent and semi-permanent hair colorants, hair styling products, such as cold waves and hair straightening products, hair tonics, hair creams and shampoos, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics, such as eye shadows, nail varnishes, lipsticks, mascaras and candles, lamp oil, scented candles, insecticides, insect repellents and propellants.

[0070] Of course, the perfume composition according to the application can also be included in a cosmetic composition or a household composition.

[0071] Another aspect of the present application relates to a perfumed product comprising a sensory workload of a fragrance composition as described above, wherein the amount of the fragrance composition is preferably in the range of 0.01 to 10 wt.-%, more preferably in the range of 0.1 to 5 wt.-%, most preferably in the range of 0.25 to 3 wt.-%, based on the total mass of the product.

[0072] In a preferred embodiment, the perfumed product is selected from the group consisting of cosmetic, hygiene and / or household products. The further preferred embodiments listed above also apply to the perfumed product of the present application.

[0073] Preferably, the perfumed product is selected from the group comprising detergents and cleaning agents, hygiene or care products, preferably in the field of body and hair care, cosmetics and household, preferably selected from the group comprising perfume extracts, eau de parfum, eau de toilette, eau de cologne, pre-shaving products, cologne splash, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, textile refreshers, ironing aids, liquid washing compositions, powdered washing compositions, laundry pretreatment preparations, fabric softeners, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, wax and polish, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, decorative makeup products, candles, lamp oil, scented candles, insecticides, insect repellents and propellants. Most preferably, the perfumed product is selected from alcoholic perfume, personal hygiene product or cleaning or care product for home use.

[0074] Furthermore, for the perfumed product of the present application, it is preferred to comprise a sensory effective amount of 1-norbornan-2-yl propan-2-one, which is sufficient to enable the consumer to obtain one or more olfactory properties selected from a more natural and / or enhanced floral character.

[0075] The above-mentioned additives, adjuvants and / or active substances are preferably not odoriferous substances. These can be, for example, preservatives, antibacterial agents, chelating agents, cleaning agents, emulsifiers, fats, etc., and in principle all substances which are used as additives, adjuvants and / or active ingredients in cosmetics, in particular in fragrance compositions, and household compositions.

[0076] Another aspect of the present application relates to a method of enhancing one or more pleasant olfactory impressions of one or more odor-pleasant compounds, in particular for enhancing and / or improving the floral and / or naturalness of one or more odor-pleasant compounds, in particular closer to lavender, wherein the compounds are different from 1-norbornan-2-yl propan-2-one, comprising or consisting of:

[0077] - mixing the odor-pleasant compounds with 1-norbornan-2-yl propan-2-one, wherein the amount of 1-norbornan-2-yl propan-2-one is sufficient to enhance and / or improve the floral and / or naturalness of the one or more odor-pleasant compounds.

[0078] Preferably, the weight ratio of 1 -norbornan-2-ylpropan-2-one to the total amount of odorant compounds different from 1 -norbornan-2-ylpropan-2-one is in the range of 1 to 1000 to 1 to 100, preferably in the range of 1 to 600 to 1 to 400.

[0079] In a preferred embodiment according to the present application, the at least one odorant compound is selected from the group of 4-methoxybenzaldehyde, borneol, isoborneol, 1 -benzopyran-2-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7-dimethyl-2,7- octadien-1 -ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenoate, camphorone-[2] (Bornan-2-on), lavandin, 3,7-dimethyloctan-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1 -ol, (2Z)-3,7-dimethylocta-2,6-dien-1 -ol, Nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7-dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1 -(propan-2-yl)cyclohex-3-en-1 -ol, p-menth-1 -en-8-ol, 2-(4-methylcyclohex-3-en-1 -yl)propan-2-ol, 4-hydroxy-3-methoxybenzaldehyde.

[0080] Preferably, 1 -norbornan-2-ylpropan-2-one is combined with one or more, particularly preferred two, three, four, five or more, of the preferred odorant compounds, particularly fragrances.

[0081] The further preferred embodiments listed above also apply to the method according to the present application.

[0082] In the following, the present application is further characterized based on examples. DETAILED DESCRIPTION

[0083] Example 1 : Synthesis of 1 -norbornan-2-ylpropan-2-one

[0084] Into a 5 liter autoclave 84 g (0.89 mol) 2-norbornene, 2329 g (17.9 mol) acetoacetate and 24 g (0.16 mol) di-tert-butylperoxide were placed and heated under 5 bar nitrogen pressure. The mixture was stirred at 155-160 °C for 1 hour. The pressure rose to 11 bar. The mixture was quickly cooled to room temperature and then evaporated on a rotary evaporator at 60-70 °C and 10-5 mbar. The residue was fractionally distilled on a 5 cm column equipped with a Thimble. The product was distilled at a top temperature of 53-99 °C and a vacuum of 0.5 mbar. 97 g of ethyl 2-norbornan-2-yl-3-oxo-butyrate according to formula II was obtained with a GC content of 86% (ratio of 2 stereoisomers 3.5:6.5).

[0085]

[0086] 1H NMR: (400 MHz, CDCl3) δ 4.26 - 4.09 (m, 4H), 3.20 (d, J = 11.7 Hz, 1H), 3.17 (d, J = 11.7 Hz, 1H), 2.27 - 2.16 (m, 4H), 2.23 (s, 3H), 2.19 (s, 3H), 2.02 - 1.96 (m, 1H), 1.90 - 1.74 (m, 1H), 1.59 - 1.41 (m, 6H), 1.35 - 1.24 (m, 4H), 1.28 (t, J = 7.2 Hz, 3H), 1.25 (t, J = 7.1 Hz, 3H), 1.22 - 1.16 (m, 2H), 1.14 (dddd, J = 11.0, 5.3, 2.5, 1.1 Hz, 2H), 1.09 (ddd, J = 9.2, 4.2, 2.7 Hz, 1H), 1.02 - 0.92 (m, 1H)

[0087] Peak 1 (NK) m / z: 43 (70), 55 (14), 66 (51), 79 (28), 94 (48), 108 (16), 130 (100), 136 (37), 153 (9), 182 (30)

[0088] Peak 2 (HK) m / z: 43 (100), 55 (19), 67 (66), 79 (41), 94 (72), 108 (29), 130 (61), 136 (78), 153 (17), 182 (99)

[0089] Into a 500 ml stirred flask, equipped with a contact thermometer, a 10 cm vigreux column, a distillation bridge, a dropping funnel and a heating mantle, 100 g (0.35 mol) of 79% 2-norbornan-2-yl-3-oxobutanoic acid ethyl ester were placed and heated to 200°C. At this temperature, 20 ml of water were added dropwise in 90 minutes, while the distillate was removed. The residue was distilled on the same apparatus. The product was distilled at a top temperature of 73-90°C and a vacuum of 5 mbar. 58 g of 1-norbornan-2-ylpropan-2-one according to formula I were obtained with a GC content of 90%.

[0090]

[0091] 1H NMR: (400 MHz, CDC13) δ 2.42 (dd, J = 16.2, 7.4 Hz, 1H), 2.26 (dd, J = 16.2, 7.7 Hz, 1H), 2.22 - 2.18 (m, 1H), 2.11 (s, 2H), 1.94 - 1.90 (m, 1H), 1.90 - 1.85 (m, 1H), 1.56 - 1.50 (m, 1H), 1.50 - 1.41 (m, 2H), 1.31 - 1.25 (m, 1H), 1.25 - 1.20 (m, 1H), 1.17 - 1.13 (m, 1H), 1.12 - 1.07 (m, 1H), 0.99 (dtd, J = 12.0, 4.5, 2.6 Hz, 1H).

[0092] m / z: 43 (100), 58 (20), 66 (75), 79 (26), 83 (33), 94 (59), 109 (24), 119 (7), 134 (17), 152 (6)

[0093] Example 2: Perfume composition

[0094] All amounts are given in weight percent.

[0095] Table 1: Examples of perfume compositions according to the application

[0096]

[0097] According to the expert panel, the addition of 2% 1-norbornan-2-ylpropan-2-one made the composition smell more floral and natural, closer to the lavender note.

Claims

1. Use of 1 -norbornan-2-ylpropan-2-one as a fragrance.

2. Use of 1 -norbornan-2-ylpropan-2-one according to claim 1 for enhancing one or more pleasant olfactory impressions of one or more fragrances, wherein the fragrances are different from 1 -norbornan-2-ylpropan-2-one; the one or more fragrances are selected from the following group: 4-methoxybenzaldehyde, borneol, isoborneol, 1 -benzopyran-2-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7-dimethyl-2,7- octadien-1 -ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenoate, bornan-2-on, lavandin, 3,7-dimethylocta-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1 -ol, (2Z)-3,7-dimethylocta-2,6-dien-1 -ol, nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7-dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1 -(propan-2-yl)cyclohex-3-en-1 -ol, p-menth-1 -ene-8-ol, 2-(4-methylcyclohex-3-en-1 -yl)propan-2-ol, 4-hydroxy-3-methoxybenzaldehyde.

3. Use according to claim 2, wherein the one or more pleasant olfactory impressions are selected from the group consisting of enhancement and / or improvement of floral and / or naturalness.

4. Use according to any one of claims 2 to 3, wherein the ratio of the total mass of the fragrance(s) to the total mass of 1 -norbornan-2-ylpropan-2-one is in the range of 1 to 1000 to 1 to 100.

5. A fragrance composition comprising or consisting of 1-norbornan-2-yl propan-2-one and at least one fragrance different from 1-norbornan-2-yl propan-2-one; wherein the fragrance is selected from the following group: 4-methoxybenzaldehyde, borneol, isoborneol, 1-benzopyran-2-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenate, bornan-2-on, lavandin, 3,7-dimethylocta-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1-ol, (2Z)-3,7-dimethylocta-2,6-dien-1-ol, nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7-dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol, p-menth-1-en-8-ol, 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol, 4-hydroxy-3-methoxybenzaldehyde.

6. The fragrance composition according to claim 5, wherein the weight ratio of 1-norbornan-2-yl propan-2-one to the total amount of fragrances different from 1-norbornan-2-yl propan-2-one is in the range of 1 to 1000 to 1 to 100.

7. The fragrance composition according to claim 5, wherein 1-norbornan-2-yl propan-2-one is used in an amount sufficient to enhance one or more pleasant olfactory impressions of one or more fragrances different from 1-norbornan-2-yl propan-2-one.

8. The fragrance composition according to claim 7, wherein 1-norbornan-2-yl propan-2-one is used in an amount to enhance or improve the floral and / or naturalness of one or more fragrances.

9. The fragrance composition according to claim 5, wherein the amount of 1-norbornan-2-yl propan-2-one is 0.01 to 50% by weight, based on the total weight of the fragrance composition.

10. The fragrance composition according to claim 6, wherein the amount of 1-norbornan-2-yl propan-2-one is 0.01 to 50% by weight, based on the total weight of the fragrance composition.

11. The fragrance composition according to claim 7, wherein the amount of 1-norbornan-2-yl propan-2-one is 0.01 to 50% by weight, based on the total weight of the fragrance composition.

12. The perfume composition according to claim 8, wherein the amount of 1- norbornan-2-ylpropan-2-one is from 0.01 to 50% by weight, based on the total weight of the perfume composition.

13. The perfume composition according to claim 9, wherein the amount of 1- norbornan-2-ylpropan-2-one is from 0.01 to 10% by weight, based on the total weight of the perfume composition.

14. The perfume composition according to claim 10, wherein the amount of 1- norbornan-2-ylpropan-2-one is from 0.01 to 10% by weight, based on the total weight of the perfume composition.

15. The perfume composition according to claim 11, wherein the amount of 1- norbornan-2-ylpropan-2-one is from 0.01 to 10% by weight, based on the total weight of the perfume composition.

16. The perfume composition according to claim 12, wherein the amount of 1- norbornan-2-ylpropan-2-one is from 0.01 to 10% by weight, based on the total weight of the perfume composition.

17. A perfumed product comprising an organoleptically effective amount of the perfume composition according to any one of claims 5 to 16, wherein the amount of the perfume composition is in the range of from 0.01 to 10% by weight, based on the total mass of the product.

18. The perfumed product according to claim 17, wherein the amount of the perfume composition is in the range of from 0.1 to 5% by weight, based on the total mass of the product.

19. The perfumed product according to claim 18, wherein the amount of the perfume composition is in the range of from 0.25 to 3% by weight, based on the total mass of the product.

20. The perfumed product according to claim 17, wherein the perfumed product is selected from the group consisting of a cosmetic product, a hygiene product and / or a household product.

21. The perfumed product according to claim 18, wherein the perfumed product is selected from the group consisting of a cosmetic product, a hygiene product and / or a household product.

22. The perfumed product according to claim 19, wherein the perfumed product is selected from the group consisting of a cosmetic product, a hygiene product and / or a household product.

23. A method of enhancing one or more pleasant olfactory impressions of one or more fragrances, wherein the fragrance is different from 1-norbornan-2-ylpropan-2-one, comprising or consisting of mixing a fragrance with 1-norbornan-2-ylpropan-2-one, wherein the amount of 1-norbornan-2-ylpropan-2-one is sufficient to enhance and / or improve the floral and / or naturalness of the one or more fragrances; the fragrance is selected from the group consisting of 4-methoxybenzaldehyde, borneol, isoborneol, 1-benzopyran-2-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-ethoxy-4-hydroxybenzaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, trans-3,7-dimethyl-2,7- octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, hexyl 2-methyl-2-butenoate, bornan-2-on, lavandin, 3,7-dimethyloct-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1-ol, (2Z)-3,7-dimethylocta-2,6-dien-1-ol, nerol acetate, alpha: (3E)-3,7-dimethylocta-1,3,7-triene, cis-beta: (3Z)-3,7-dimethylocta-1,3,6-triene, trans-beta: (3E)-3,7-dimethylocta-1,3,6-triene, 4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol, p-menth-1-ene-8-ol, 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol, 4-hydroxy-3-methoxybenzaldehyde.

24. The method according to claim 23, for enhancing and / or improving the floral and / or naturalness of one or more fragrances.

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