1-Norbornan-2-yl propane-2-one as a fragrance

Abstract

The present invention proposes the use of 1-norbornan-2-yl propane-2-one as a fragrance.

Description

Technical Field

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

Background Art

[0002] In the perfume industry, there is always a demand for the creation of new fragrances. However, the creation of new fragrances and fragrance compositions involves many challenges. For example, in order to meet specific market needs and provide products that match the specific profiles required by customers, it is necessary to select specific compositions of a small number of fragrances from a virtually infinite number of possible structures known from the prior art. Suitable fragrances exhibit very beneficial properties, but when combined with other fragrances, they may exhibit unfavorable odor aspects due to being unpleasant, making them difficult or even impossible to use for specific purposes.

[0003] The second important challenge relates to the need to provide fragrance compositions that not only match a specific odor profile but also have so-called second beneficial properties. In fact, many fragrance compositions known in the market not only have significant drawbacks in use such as poor solubility and low stability to storage, but also have not been successful in subjective issues such as richness and charisma. Furthermore, many of the known fragrance compositions require high dosages to obtain the desired odor results. Another requirement for today's fragrances is high biodegradability and dermatological and toxicological safety. Therefore, there is a particular need to provide fragrances that have a large effect on other fragrances even in small amounts, rather change the impression of unpleasant odors into positive ones, and / or enhance the impression of pleasant odors.

Summary of the Invention

Problems to be Solved by the Invention

[0004] Accordingly, the underlying problem of the present invention was to provide a novel perfume having the ability to enhance the positive and beneficial perfume aspects of other perfumes and / or (simultaneously) reduce, suppress and / or mask unwanted and unpleasant perfume aspects. In particular, the novel perfume should also have the characteristics of improving the stability, solubility and overall performance of other perfumes and reducing the required dosage. Finally, it is required that the perfume composition itself has excellent biodegradability and is harmless to humans and the environment.

Means for Solving the Problem

[0005] This problem is solved by using 1-norbornan-2-yl propan-2-one as a perfume.

[0006] The 1-norbornan-2-yl propan-2-one used according to the present invention may exist in the form of any stereoisomer or as a mixture of any stereoisomers.

[0007] What has been said herein about 1-norbornan-2-yl propan-2-one, in particular the advantages described herein, also apply to mixtures of stereoisomers of 1-norbornan-2-yl propan-2-one used or employed according to the present invention.

[0008] 1-Norbornan-2-yl propan-2-one is extremely unique and clearly different from and superior to those of known odor substances in terms of olfactory properties. The suitability of 1-norbornan-2-yl propan-2-one as a perfume was not previously known. Therefore, it is particularly surprising that a perfume with valuable and interesting complex olfactory properties has been discovered in a field that has already been well studied.

[0009] 1-Norbornan-2-yl propan-2-one has the following structural formula

[0010]

Chemical formula

[0011] As described above, its suitability as a fragrance is unknown. Similarly, an exact odor description is not available, but according to the inventors, 1-norbornan-2-yl propan-2-one has a fruity and wintergreen odor similar to isoamyl acetate.

[0012] As a result, the inventors have made the surprising discovery that 1-norbornan-2-yl propan-2-one is suitable as a fragrance and produces a special effect in combination with pleasant-smelling compounds in small doses. For this purpose, these compounds are different from 1-norbornan-2-yl propan-2-one.

[0013] In a preferred embodiment according to the invention, 1-norbornan-2-yl propan-2-one is used to enhance one or more pleasant olfactory impressions of one or more pleasant-smelling compounds, and for this purpose, this compound / these compounds are different from 1-norbornan-2-yl propan-2-one. Preferably, the one or more pleasant olfactory impressions of the one or more pleasant-smelling compounds are selected from enhancing and / or improving floweriness and / or naturalness, especially enhancing and / or improving floweriness and / or naturalness closer to lavender. That is, 1-norbornan-2-yl propan-2-one preferably enhances or improves the floweriness and / or naturalness of pleasant-smelling compounds. In particular, 1-norbornan-2-yl propan-2-one shifts the olfactory impression of these substances more towards lavender.

[0014] As used herein, the singular forms "a", "an", and "the" include plural references unless the context clearly dictates otherwise. For example, the term "compound" or "at least one compound" may include a plurality of compounds including mixtures thereof. Also, the plural forms include singular embodiments unless the context clearly dictates otherwise. For example, the term "one or more pleasant-smelling compounds" also includes embodiments using only one pleasant-smelling compound.

[0015] It is particularly surprising that 1-norbornan-2-yl propan-2-one, used according to the present invention, can impart a very complex and variable overall sensory impression that can usually only be achieved by a mixture of several components (such as essential oils or spice mixtures) in other ways.

[0016] Beyond the first, i.e., olfactory properties, 1-norbornan-2-yl propan-2-one has further positive second properties, in particular, high substantivity compared to fragrances with similar olfactory properties, as well as high stability, high extensibility, and biodegradability in certain media and preparations.

[0017] It has also been recognized that 1-norbornan-2-yl propan-2-one can function excellently as a so-called booster (amplifier; enhancer). Preferably, 1-norbornan-2-yl propan-2-one is used as a booster for one or more pleasant olfactory impressions of one or more pleasant-smelling compounds. In other words, by using 1-norbornan-2-yl propan-2-one together with other pleasant-smelling compounds, their pleasant-smelling notes are enhanced.

[0018] Furthermore, 1-norbornan-2-yl propan-2-one used according to the present invention can enhance the strength of the fragrance composition and round off the overall odor of the resulting mixture. Thus, the compounds described herein can be used to impart more floral and / or natural notes to other compounds, particularly compounds with at least one or two or more pleasant olfactory impressions. Furthermore, 1-norbornan-2-yl propan-2-one is suitable as an agent for enhancing the substantivity and / or retention power of the fragrance composition.

[0019] In the context of the present invention, the "compound with a pleasant odor" is generally understood as a substance that evokes one or two or more pleasant odor impressions, whether as a first olfactory note or as a second / dependent olfactory note. The terms "compound with a pleasant odor" and "fragrance" are used interchangeably in the context of the present invention.

[0020] Preferably, the one, two or more or all of the compounds with a pleasant odor different from 1-norbornan-2-yl propan-2-one are fragrances having a molar mass in the range of 150 g / mol to 285 g / mol, particularly alcohols, aldehydes, ketones, ethers, esters and carboxylates and carboxylic acid esters having a molar mass in the range of 150 g / mol to 285 g / mol, selected from the group consisting of.

[0021] More preferably, the one, two or more or all of the pleasant smell compounds are 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, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, 2-methyl-2-butenoic acid hexyl ester, boran-2-one, lavandin, 3,7-dimethyloct-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1-ol, (2Z)-3,7-dimethyloct-2,6-dien-1-ol, nerol acetate, α:(3E)-3,7-dimethylocta-1,3,7-triene, cis-β:(3Z)-3,7-dimethylocta-1,3,6-triene, trans-β:(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 and 4-hydroxy-3-methoxybenzaldehyde.

[0022] In a preferred embodiment according to the present invention, the ratio of the total mass of the pleasant smell compound to the total mass of -(methoxymethyl)-2-methyl-benzene is in the range of 1:1000 to 1:100, preferably 1:600 to 1:400.

[0023] 1-Norbornan-2-ylpropan-2-one can be used in various products and can be used as a single fragrance, but it can also be particularly advantageously combined with other pleasant smell compounds, especially in different proportions, to form a fragrance mixture, and can also create a novel and original perfume composition.

[0024] Accordingly, one aspect of the present invention also relates to a fragrance mixture containing 1-norbornan-2-yl propane-2-one and optionally further constituents (such as solvents).

[0025] The fragrance composition according to the present invention comprises or consists of 1-norbornan-2-yl propane-2-one and at least one further pleasant-smelling compound different from 1-norbornan-2-yl propane-2-one. Preferably, the fragrance composition according to the present invention comprises or consists of 1-norbornan-2-yl propane-2-one and two or more further pleasant-smelling compounds different from 1-norbornan-2-yl propane-2-one. More preferably, the fragrance composition according to the present invention comprises or consists of 1-norbornan-2-yl propane-2-one and three or more further pleasant-smelling compounds different from 1-norbornan-2-yl propane-2-one. Most preferably, the fragrance composition according to the present invention comprises or consists of 1-norbornan-2-yl propane-2-one and four or more further pleasant-smelling compounds different from the 1-norbornan-2-yl propane-2-one fragrance.

[0026] The 1-norbornan-2-yl propane-2-one according to the present invention is usually used in a functionally effective amount, i.e., the total amount that exerts a functional effect.

[0027] Preferably, the weight ratio of 1-norbornan-2-yl propane-2-one to the total amount of pleasant-smelling compounds different from 1-norbornan-2-yl propane-2-one is in the range of 1:1000 to 1:100, preferably 1:600 to 1:400.

[0028] In a preferred embodiment according to the present invention, 1-norbornyl propan-2-one is present in the fragrance composition in a functionally effective amount sufficient to enhance one or more pleasant olfactory impressions of one or more compounds having a pleasant odor different from 1-norbornyl propan-2-one, in particular in a functionally effective amount sufficient to enhance or improve the floral and / or natural character, in particular the floral and / or natural character closer to lavender, of one or more compounds having a pleasant odor.

[0029] Examples of compounds having a pleasant odor, in particular fragrances, which can advantageously be combined with 1-norbornyl propan-2-one in the context of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N.J. 1969, self-published, or in K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0030] Specifically, the following may be mentioned: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures. Further specific examples are as follows. Ambergris tincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoin resinoid; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Broccoli leaf oil; Cabbage rose oil; cade oil; Calamus oil; Camphor oil; Cananga oil; Cardamom oil; Cascara oil; Cassia oil; Cassie absolute; Castoreum absolute; Cider leaf oil; Cider wood oil; Cistus oil; Citronella oil; Citron oil; Copaiba balsam; Copaiba balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Odebrecht absolute; Oak moss absolute; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Galbanum oil; Galbanum resin; Geranium oil; Grapefruit peel oil; Guaiac wood oil; Gurjun balsam; Gurjun balsam oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Calamus oil; Chamomile oil blue; Chamomile oil roman; Carrot seed oil; Cascara oil; Pine needle oil; Spearmint oil; Caraway oil; Labdanum oil; Labdanum absolute; Labdanum resin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Labège oil; Lime oil distilled; Lime oil expressed; Linaloe oil; Litsea cubeba oil; Bay leaf oil; Mace oil; Marjoram oil; Mandarin oil; Massoia bark oil; Mimosa absolute; Musk grain oil; Musk tincture; Muscat sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange flower absolute; Orange oil; Oregano oil; Palmarosa oil; Patchouli oil; Egoma oil;Peruvian balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil; peppermint oil; pepper oil; allspice oil; pine oil; poppy oil; rose absolute; rosewood oil; rose oil; rosemary oil; sage oil Dalmatian; sage oil Spanish; sandalwood oil; celery seed oil; spicy lavender oil; star anise oil; styrax oil; tagetes oil; fir needle oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; wine yeast oil; mugwort oil; wintergreen oil; ylang-ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil and their fractions, or components separated therefrom;

[0031] Individual odoriferous substances from the group of hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane; Individual odoriferous substances from the group of 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; mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methylenheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; Individual odor substances from the group of 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; 1-(1-methoxy-propoxy)-(E / Z)-3-hexene; Individual odor substances from the group of 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; 6-methyl-5-hepten-2-one; Individual odor substances from the group of 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; Individual odor substances from the group of 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-octadecadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile; Individual odor substances from the group of 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; 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-octynoate; methyl 2-nonynoate; allyl 2-isoamyloxyacetate; methyl 1,3,7-trimethyl-2,6-octadien-oate; 4-methyl-2-pentyl crotonate; Individual odor substances from the group of acyclic terpene alcohols, such as geraniol; nerol; lavandulol; 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-octatriene-3-ol; 2,6-dimethyl-2,5J-octatriene-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; Individual odor substances from the group of acyclic terpene aldehydes and ketones, such as citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; geranial, dimethyl acetal and diethyl acetal of neral, Individual odor substances from the group of cyclic terpene alcohols, such as menthol; isopulegol; α-terpineol; terpinolene-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambroxanol; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates, 3-methyl-2-butenoate; Individual odor substances from the group of cyclic terpene aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methyliounone; β-n-methyliounone; α-isomethyliounone; 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-naphthalene-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; acetylated cedrowood oil (methyl cedryl ketone); Individual odor substances from the group of 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; 4-cyclohexylbutan-2-ol; Individual odor substances from the group of cycloaliphatic alcohols, such as 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)-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; Individual odor substances from the group of cyclic and cycloaliphatic 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[2,1-b]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; Individual odor substances from the group of cyclic 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-cyclopentadecenone; 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; Individual odor substances from the group of cycloaliphatic 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; Individual odor substances from the group of cycloaliphatic 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) ketone; Individual odor substances from the group of esters of cyclic alcohols, 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-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, resp. 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; Individual odor substances from the group of esters of cycloaliphatic alcohols, such as 1-cyclohexylethyl crotonate; Individual odor substances from the group of esters of cycloaliphatic 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; ethyl 2-methyl-1,3-dioxolan-2-acetate; Individual odor substances from the group of aromatic aliphatic alcohols, such as benzyl alcohol; 2-phenylethanol; 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; Individual odor substances from the group of 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; 4-methoxybenzyl acetate; Individual odor substances from the group of 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-dioxin; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin; and individual odor substances from the group of aromatic aliphatic aldehydes, such as 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; 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; Individual odor substances from the group of aromatic and araliphatic ketones, such as 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-benzofuranylethanone); benzophenone; 1,1,2,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-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´,6´,8´,8´-hexamethyl-2-acetonaphthone; Individual odor substances from the group of 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; 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; phenyl ethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate; Individual odor substances from the group of 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; Individual odor substances from the group of 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-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; ethylene-1,12-dodecanedioate; ethylene-1,13-tridecanedioate; 2,3-dihydrocoumarin; octahydrocoumarin.

[0032] In a further preferred embodiment of the present invention, 1-norbornan-2-yl propane-2-one is preferably combined with one or more, particularly preferably two, three, four, five or more pleasant-smelling compounds.

[0033] 1-Norbornan-2-yl propane-2-one used according to the present invention advantageously (at least partially) achieves an odor enhancement of the olfactory impression of a pleasant smell.

[0034] Preferably, the one, two or more or all of the pleasant-smelling compounds different from 1-norbornan-2-yl propane-2-one are fragrances having a molar mass in the range of 150 g / mol to 285 g / mol, particularly alcohols, aldehydes, ketones, ethers, esters, and carboxylates and carboxylic acid esters having a molar mass in the range of 150 g / mol to 285 g / mol, selected from the group consisting of.

[0035] In a more preferred embodiment according to the present invention, the one, two or more or all of the pleasant-smelling compounds are 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, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, 2-methyl-2-butenoic acid hexyl ester, bornan-2-one, 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, α:(3E)-3,7-dimethylocta-1,3,7-triene, cis-β:(3Z)-3,7-dimethylocta-1,3,6-triene, trans-β:(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 and 4-hydroxy-3-methoxybenzaldehyde.

[0036] Preferably, 1-norbornan-2-ylpropan-2-one is combined with one or two or more, particularly preferably two, three, four, five or six or more pleasant-smelling compounds.

[0037] The perfume composition containing 4-cyclohexyl-2-butanol is advantageously used in the blending of perfumes in a liquid state, either as a stock solution or diluted with a solvent. Suitable solvents for this purpose are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, and the like.

[0038] Furthermore, the perfume composition according to the present invention can be adsorbed on a carrier that ensures both a fine distribution of the perfume in the product and a controlled release during use. Such carriers can be porous inorganic materials, such as light sulfate, silica gel, zeolite, plaster, clay, clay granules, cellular concrete, or organic materials, such as wood, cellulose-based substances, sugar, dextrin (e.g., maltodextrin), or plastics, such as PVC, polyvinyl acetate, or polyurethane. The combination obtained from the composition according to the present invention and the carrier substance is also understood as the perfume composition according to the present invention.

[0039] The perfume composition according to the present invention can also be microencapsulated, spray-dried, used as an inclusion complex or an extruded product, and in this form, for example, added to the product to be perfumed.

[0040] If necessary, the properties of the composition thus modified can be further optimized by a so-called "coating" with a suitable material from the perspective of a more targeted release of the perfume. For this purpose, waxy plastics such as polyvinyl alcohol are preferably used. As a result, the product thus obtained becomes an article according to the present invention.

[0041] Preferably, the amount of 1-norbornan-2-yl propan-2-one is in the range of 0.01 to 50% by weight based on the total weight of the fragrance composition. More preferably, the amount of 1-norbornan-2-yl propan-2-one is in the range of 0.01 to 10% by weight based on the total weight of the fragrance composition. Even more preferably, the amount of 1-norbornan-2-yl propan-2-one is in the range of 0.1 to 2.5% by weight based on the total weight of the fragrance composition.

[0042] The perfume composition according to the present invention can conveniently be used, in concentrated form, in solution, or in the improved form described above, for the manufacture of perfumed articles according to the present invention. Specific examples of said articles are: B. perfume extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, pre-shave products, splash cologne and aromatic refreshment towels, as well as acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, polishing emulsions, solid and liquid toilet cleaners, powder and foam carpet cleaners, fabric perfumes, ironing aids, liquid detergents, powder detergents, perfume additives, pre-washing treatment agents, such as bleaching agents, soaking agents, stain removers, softening finishes, laundry soaps, laundry tablets, as well as bactericidal perfumes, aerosol sprays, waxes and polishes in the form applied to liquid, gel-like or solid carriers, such as furniture polishes, floor waxes, shoe creams, as well as personal care products such as solid and liquid soaps, shower gels, shampoos, beard soaps, beard foams, bath oils, water-in-oil, oil-in-water and water-in-oil-in-water cosmetic emulsions, such as skin creams and skin lotions, face creams and face lotions, sun protection creams and sun protection lotions, after-sun creams and after-sun lotions, hand creams and hand lotions, foot creams and foot lotions, depilatory creams and depilatory lotions, aftershave creams and aftershave lotions, sunburn creams and sunburn lotions, hair care products, such as hair sprays, hair gels, hair setting lotions, hair conditioners, permanent hair dyes, semi-permanent hair dyes, hair styling agents, such as cold wave agents, hair straightening agents, hair lotions, hair creams, hair lotions, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics, such as eye shadows, nail polishes, lipsticks, mascaras, as well as products such as candles, lamp oils, incense sticks, insecticides, repellents, fuels, etc.

[0043] Of course, the fragrance composition according to the present invention can also be included in cosmetic compositions and household compositions.

[0044] A further aspect of the present invention relates to a scented product containing the above-mentioned fragrance composition in a sensory effective amount, and the amount of the fragrance composition calculated based on the total mass of the product is preferably in the range of 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and most preferably 0.25 to 3% by weight.

[0045] In a preferred embodiment, the scented product is selected from cosmetics, hygiene products and / or household products. The further preferred embodiments listed above are also applicable to the scented products of the present invention.

[0046] Preferably, the scented product is hereinafter selected from the group consisting of detergents and cleaning agents, hygiene products or care products, preferably body care and hair care, products in the fields of cosmetics and household, preferably perfume extracts, eau de parfum, eau de toilette, aftershave lotion, eau de cologne, pre-shave products, splash cologne, scented freshening tissues, acidic, alkaline or neutral cleaning agents, fabric fragrances, ironing aids, liquid detergents, powder detergents, pre-wash treatment agents, fabric softeners, cleaning tablets, disinfectants, surface disinfectants, fragrances, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, sunburn creams and lotions, hair care products, hair care products, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels. Most preferably, the scented product is selected from alcoholic perfumes, personal hygiene products, cleaning or care products for household use.

[0047] Furthermore, it is preferred for the fragrance-containing product according to the present invention that 1-norbornan-2-yl propan-2-one is contained in a sensorial effective amount sufficient to have one or more olfactory properties selected from the group consisting of more naturalness and / or enhanced floral notes for the consumer.

[0048] The above-mentioned additives, auxiliaries and / or active substances are preferably not odor-emitting substances. These may be, for example, preservatives, antibacterial agents, chelating agents, detergents, emulsifiers, fats and oils, etc., and in principle, all substances used as additives, auxiliaries and / or active ingredients in cosmetics, particularly fragrance compositions, and / or household compositions may be used.

[0049] Another aspect of the present invention relates to a method for enhancing one or more pleasant olfactory impressions of one or more pleasant-smelling compounds, particularly for enhancing and / or improving the floral and / or natural character, particularly the lavender-like floral and / or natural character, of one or more pleasant-smelling compounds, wherein the compound is different from 1-norbornan-2-yl propan-2-one, and the method comprises the following steps: - A step of mixing the pleasant-smelling compound with 1-norbornan-2-yl propan-2-one, wherein the amount of 1-norbornan-2-yl propan-2-one is an amount sufficient to enhance and / or improve the floral and / or natural character of the one or more pleasant-smelling compounds. The method comprises or consists of the above step.

[0050] Preferably, the weight ratio of 1-norbornan-2-yl propan-2-one to the total amount of the pleasant-smelling compound different from 1-norbornan-2-yl propan-2-one is in the range of 1:1000 to 1:100, preferably 1:600 to 1:400.

[0051] In a preferred embodiment according to the present invention, at least one of the pleasant-smelling compounds 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, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, 2-methyl-2-butenoic acid hexyl ester, boran-2-one, 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, α:(3E)-3,7-dimethylocta-1,3,7-triene, cis-β:(3Z)-3,7-dimethylocta-1,3,6-triene, trans-β:(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, and 4-hydroxy-3-methoxybenzaldehyde.

[0052] Preferably, 1-norbornan-2-yl propan-2-one is combined with one or more, particularly preferably two, three, four, five, or six or more pleasant-smelling compounds, especially in combination with a fragrance.

[0053] The more preferred embodiments listed above are also applicable to the method of the present invention.

[0054] Hereinafter, the present invention will be further characterized based on examples.

Examples

[0055] Example 1: Synthesis of 1-Norbornan-2-ylpropan-2-one

[0056] 84 g (0.89 mol) of 2-norbornene, 2329 g (17.9 mol) of ethyl acetoacetate and 24 g (0.16 mol) of di-tert-butyl peroxide were placed in a 5-liter autoclave and heated under a nitrogen pressure of 5 bar. The resulting mixture was stirred at 155 - 160 °C for 1 hour. The pressure was raised to 11 bar. The resulting mixture was rapidly cooled to room temperature and then evaporated on a rotary evaporator at 60 - 70 °C and 10 - 5 mbar. The residue obtained was fractionated on a 5 cm column equipped with Raschig rings. The product was distilled at a maximum temperature of 53 - 99 °C and a vacuum of 0.5 mbar. 97 g of ethyl 2-norbornan-2-yl-3-oxo-butanoate according to formula II (two stereoisomers in a ratio of 3.5:6.5) with a GC content of 86% was obtained.

[0057]

Chemical formula

[0058] 100 g (0.35 mol) of ethyl 79% 2-norbornan-2-yl-3-oxobutanoate was placed in a 500 ml stirrer equipped with a contact thermometer, a 10 cm Vigreux column, a distillation bridge, a dropping funnel and a heating hood, and heated to 200 °C. At this temperature, 20 ml of water was added dropwise over 90 minutes while removing the distillate in parallel. The resulting residue was distilled in the same apparatus. Distillation was carried out at a maximum temperature of 73 - 90 °C and a vacuum of 5 mbar. 58 g of 1-norbornan-2-ylpropan-2-one according to formula I with a GC content of 90% was obtained.

[0059]

Chemical formula

[0060] Example 2: Flavor composition All amounts are shown in weight %.

[0061]

Table 1

Claims

Claim 1 Use of 1-norbornan-2-yl propane-2-one as a fragrance. Claim 2 Use for enhancing one or more pleasant olfactory impressions of one or more compounds with a pleasant odor, for which purpose these compounds are different from 1-norbornan-2-yl propane-2-one, the use of 1-norbornan-2-yl propane-2-one according to Claim 1. Claim 3 The use according to Claim 2, wherein the one or more pleasant olfactory impressions are selected from enhancing and / or improving floralness and / or naturalness. Claim 4 The one or more compounds with a pleasant odor different from 1-norbornan-2-yl propane-2-one are fragrances having a molar mass in the range from 150 g / mol to 285 g / mol, in particular alcohols, aldehydes, ketones, ethers, esters and carboxylates and carboxylic acid esters having a molar mass in the range from 150 g / mol to 285 g / mol, the use according to any one of Claims 1 to 3. Claim 5 The use according to any one of claims 1 to 4, wherein the one or more pleasant-smelling compounds are 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, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, 2-methyl-2-butenoic acid hexyl ester, boran-2-one, 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, α:(3E)-3,7-dimethylocta-1,3,7-triene, cis-β:(3Z)-3,7-dimethylocta-1,3,6-triene, trans-β:(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, and 4-hydroxy-3-methoxybenzaldehyde.

6. The use according to any one of claims 1 to 5, wherein the ratio of the total mass of the pleasant-smelling compound to the total mass of 1-norbornan-2-yl propan-2-one is in the range of 1:1000 to 1:

100.

7. A fragrance composition comprising 1-norbornan-2-yl propan-2-one and at least one additional pleasant-smelling compound different from 1-norbornan-2-yl propan-2-one, or consisting of these.

8. The fragrance composition according to claim 7, wherein the weight ratio of 1-norbornan-2-yl propan-2-one to the total amount of the pleasant-smelling compounds different from 1-norbornan-2-yl propan-2-one is in the range of 1:1000 to 1:

100.

9. The amount of 1-norbornan-2-yl propan-2-one is an amount sufficient to enhance one or more pleasant olfactory impressions of one or more compounds with a pleasant odor different from 1-norbornan-2-yl propan-2-one, in particular, an amount sufficient to enhance or improve the floral and / or natural character of one or more compounds with a pleasant odor, the fragrance composition according to claim 7 and / or 8.

10. The amount of 1-norbornan-2-yl propan-2-one is in the range of 0.01 to 50% by weight based on the total weight of the fragrance composition, the fragrance composition according to at least one of claims 7 to 9.

11. The amount of 1-norbornan-2-yl propan-2-one is in the range of 0.01 to 10% by weight based on the total weight of the fragrance composition, the fragrance composition according to at least one of claims 7 to 9.

12. The one or more pleasant-smelling compounds are 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, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, trans-3,7-dimethyl-2,7-octadien-1-ol, geranyl acetate, cis-3-hexenyl isovalerate, hexyl acetate, hexyl butyrate, hexyl isobutyrate, 2-methyl-2-butenoic acid hexyl ester, boran-2-one, lavandin, 3,7-dimethyloct-1,6-dien-3-ol, 5-methyl-2-(propan-2-yl)cyclohexan-1-ol, (2Z)-3,7-dimethyloct-2,6-dien-1-ol, nerol acetate, α:(3E)-3,7-dimethyloct-1,3,7-triene, cis-β:(3Z)-3,7-dimethyloct-1,3,6-triene, trans-β:(3E)-3,7-dimethyloct-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, and 4-hydroxy-3-methoxybenzaldehyde, the fragrance composition according to at least one of claims 7 to 11.

13. A fragrance-containing product comprising the fragrance composition according to claims 7 to 12 in a sensory-effective amount, wherein the amount of the fragrance composition calculated based on the total mass of the product is preferably in the range of 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and most preferably 0.25 to 3% by weight, the fragrance-containing product.

14. The fragrance-containing product according to claim 13, wherein the product is selected from cosmetics, hygiene products and / or household products.

15. A method for enhancing one or more pleasant olfactory impressions of one or more pleasant-smelling compounds, in particular for enhancing and / or improving the floral and / or natural character of one or more pleasant-smelling compounds, wherein one or more of said compounds are different from 1-norbornan-2-yl propane-2-one, said method comprising the following steps: - mixing said pleasant-smelling compound with 1-norbornan-2-yl propane-2-one, wherein the amount of 1-norbornan-2-yl propane-2-one is an amount sufficient to enhance and / or improve the floral and / or natural character of one or more pleasant-smelling compounds comprising or consisting of said step.

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