Compositions containing 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or its esters or ethers, and their use as fragrance chemicals

Abstract

The present invention relates to the use of a composition comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof and 3-isopropyl-6-methyl-cyclohex-2-en-1-one or the use of 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof as a fragrance chemical or for modifying and / or enhancing the fragrance of a composition. The present invention further relates to compositions comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof and 3-isopropyl-6-methyl-cyclohex-2-en-1-one, to certain compositions comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol, and to certain esters or ethers of 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol.

Description

[Technical field]

[0001] The present invention relates to the use of a composition comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof and 3-isopropyl-6-methyl-cyclohex-2-en-1-one or the use of 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof as a fragrance chemical or for modifying and / or enhancing the fragrance of a composition. The present invention further relates to compositions comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol or certain esters or ethers thereof and 3-isopropyl-6-methyl-cyclohex-2-en-1-one, to certain compositions comprising 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol, and to certain esters or ethers of 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol. [Background technology]

[0002] Aroma chemicals, especially fragrances, are of great interest in the field of cosmetics and cleaning and laundry compositions. Naturally derived fragrances are often expensive, often have limited availability, and vary in content, purity, etc. due to variations in environmental conditions. Therefore, to avoid these undesirable factors, there is great interest in producing synthetic substances that have sensory properties similar to those of more expensive natural fragrances or that have new and interesting sensory profiles.

[0003] Although many aroma chemicals already exist, new ingredients are constantly needed to be able to meet many of the desired properties in the most diverse fields of application. As such, first of all, sensory properties must be mentioned, i.e. the compounds must have favorable odor (olfactory) or taste properties. In addition to this, aroma chemicals must also have favorable secondary properties, such as an efficient preparation method, the possibility of synergizing with other aroma chemicals to show a better sensory profile, a wider range of compositions and higher stability under certain application conditions, higher extendability and / or better staying power.

[0004] However, it is very difficult to search for substances with specific sensory properties, such as a specific smell, because even small changes in chemical structure can significantly change the smell as well as the taste, etc. Thus, the search for new fragrances and flavors is often a difficult and arduous task, where it is not even known whether a substance with the desired smell and / or taste will actually be found.

[0005] Moreover, as a result of the foreseeable depletion of fossil fuels, as well as the ecological and economic imperative to reduce waste and CO2 emissions, it becomes increasingly important to maximize the efficiency of industrial production processes and at the same time to make a more rational use of the unavoidable organic by-products, rather than simply using them as fuel or combustion material, as is currently done in most cases: even if this fueling / combustion is used to produce energy and serves some purpose, this use is unsatisfactory, since it wastes potentially valuable substances.

[0006] 3-Isopropyl-6-methyl-cyclohex-2-en-1-one, also known as carbenone, is a monocyclic monoterpene that is said to have a minty odor.

[0007] 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol is also known as 2-hydroxy-1,4-cineole.

[0008] JP 01-261327 A relates to perfume compositions containing 1-menthol and 2-hydroxy-1,8-cineole or 2-hydroxy-1,4-cineole. The use of 2-hydroxycineole enhances the cooling sensation of menthol and improves its persistence. Even as such, however, they are said to lack interesting characteristics from the fragrant point of view.

[0009] US Patent No. 4,853,089 relates to a method for purifying exo-2-hydroxy-1,4-cineole contaminated with ketones. In Examples 6 and 7, mixtures containing, inter alia, 75.6 or 67.7% by weight of exo-2-hydroxy-1,4-cineole and 10.3 or 12.8% by weight of carbenones are subjected to said purification process.

[0010] M. Mertens et al. describe the volatile components of frankincense in Flavour Fragr. J. 2009, 24, 279-300. The volatiles found in pyrolyzed B. carteri are reported to contain, among others, 2-hydroxy-1,4-cineole.

[0011] SNG Arg et al., in Phytochemistry 1989, 28(2), 634-636, describe the essential oil from the rhizomes of Ferula Jaeschkeana. One of its constituents is 2β-hydroxy-1,4-cineole.

[0012] AFM Barton et al., J. Agric. Food Chem. 2010, 58, 10147-10155, describe the synthesis and herbicidal activity of various cineole derivatives. In particular, the conversion of 2-hydroxy-1,4-cineole to its various esters and ethers is described.

[0013] 2-Hydroxy-1,4-cineole is the direct precursor in the synthesis of the herbicide cinmethylin. 2-Hydroxy-1,4-cineole is the dihydrogen amine of 1,4-terpinen-4-ol with the following formula: [ka] to epoxide compounds followed by acid-catalyzed rearrangement. This route is described, for example, in WO 2018 / 210662, EP 0081892 or EP 0081893. Isolation and purification of 2-hydroxy-1,4-cineole results in a waste stream containing carbenox as the main component and traces of 2-hydroxy-1,4-cineole. Summary of the Invention

[0014] The object of the present invention was to provide new aroma chemicals. Moreover, these substances should be capable of being combined with other aroma chemicals to create new advantageous sensory profiles. Furthermore, the process for preparing such new aroma chemicals should be easy and efficient so as to allow fast, economical and environmentally friendly production. However, in particular, they should be obtained from by-products of industrial processes that would otherwise be discarded or taken to low-value applications such as energy production.

[0015] These and further objects are achieved by compositions comprising compounds of formulae (I) and (II) as shown below, by specific compositions comprising only the compound of formula (I) and by specific compound (I). The compositions comprising compounds of formulae (I) and (II) are obtainable by the production of cinmethylin from the epoxide compounds shown above, which in turn are obtained from terpinen-4-ol, a compound obtainable from natural renewable resources.

[0016] In one aspect, the present invention provides a method for producing a method for treating a cancer cell comprising: (a) Formula (I) [ka] [In the formula, R 1 is hydrogen, C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl, or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I); (b) Formula (II) [ka] or a mixture of different stereoisomers thereof The present invention relates to the use of a composition comprising the compound (hereinafter also referred to as composition A) as a fragrance chemical.

[0017] The present invention also relates to the use of composition A as defined above for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition.

[0018] The present invention further relates to a composition A comprising a compound of formula (I), or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I); and a compound of formula (II), or a stereoisomer thereof, or a mixture of the different stereoisomers thereof.

[0019] The present invention further relates to a composition (hereinafter also referred to as composition B) comprising a compound of formula (I), or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I), and at least one further component selected from the group consisting of aroma chemicals different from compounds (I) and (II), non-aroma chemical carriers, antioxidants, and deodorant actives; in particular selected from the group consisting of aroma chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants, and deodorant actives; when the composition comprises menthol, hydroxycarbomenthone, 3,7-dimethyl-2,6-octadiene, krypton, p-menthane-1,2-diol, dichloromethane, tetrahydrofuran, dimethylformamide, hexane, or chloroform, R 1 is not hydrogen; if the composition contains dichloromethane or hexane, R 1 is not acetyl (methylcarbonyl; -C(O)CH3), and R 1 is hydrogen and the aroma chemical different from compound (I) is a compound of formula (II) as defined in claim 1, whereby the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 3:1 to 1:>1; and the use of compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I), as an aroma chemical; or for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition, wherein the use comprises the addition of R 1 is hydrogen; and the use does not include the use of a compound of formula (I) where R is hydrogen; for modifying and / or enhancing the aroma of menthol or for modifying and / or enhancing the aroma of an essential oil obtained from the rhizomes of Ferula Jaeschkeana. 1The present invention relates to the use of compounds of formula (I) in which R is hydrogen.

[0020] The invention further relates to a method for imparting an aroma, preferably a fragrance, to a composition, in particular to an (other) ready-to-use composition, which comprises incorporating, into the composition to be aromatized, in particular to be fragranced, compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I); or incorporating both compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or one or more stereoisomers of these compounds (I), and compound (II) or a mixture of its stereoisomers or its different stereoisomers.

[0021] The present invention also relates to a method for modifying the odor characteristics of an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, which comprises incorporating into the aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I); or incorporating both compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or one or more stereoisomers of these compounds (I), and compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers.

[0022] The present invention further relates to a method for preparing an aromachemical composition, in particular a fragrance composition, in particular a ready-to-use fragrance composition, which comprises incorporating into the composition, in particular a ready-to-use composition, compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I); or incorporating both compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or one or more stereoisomers of these compounds (I), and compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers.

[0023] The present invention further provides compound (I), 1 is C1-C3 alkyl, formyl, or ethylcarbonyl] and the use of this compound (I) as an aroma chemical; or for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] Definition: In the context of the present invention, the term "aroma" refers to sensory properties and includes smell and / or flavor.

[0025] The term "aroma chemical" means a substance [i.e. in the present case a substance mixture / composition of compounds (I) and (II)] used to obtain an aroma impression (the term "aroma impression" is used interchangeably herein with the term "note"), including its use to obtain an olfactory and / or flavor impression. The term "olfactory impression" or "odor impression" (used interchangeably herein) means an odor impression without a positive or negative judgement, and as used herein, the term "scent impression" or "fragrance impression" (used interchangeably herein) relates to an odor impression that is generally perceived as pleasant. Thus, "fragrance" or "scent" means an aroma chemical that induces a primarily pleasant odor impression. Flavor means an aroma chemical that induces a taste impression.

[0026] The term "aroma profile" means the overall aroma impression of an aroma chemical, which is made up of the individual aroma impressions of the aroma chemicals.

[0027] The term "fragrance composition" as used herein refers to a composition that induces an aroma. The term fragrance composition includes an "odor composition" and / or a "flavor composition." An odor composition is a composition that induces primarily an odor impression, and a flavor composition is a composition that induces primarily a taste impression.

[0028] The term olfactory composition includes "fragrance compositions" or "scent compositions" (used interchangeably herein) that primarily induce an olfactory impression that is generally perceived as pleasant.

[0029] "Pleasant odor", "pleasant odor impression", "pleasant odor characteristics", "pleasant odor impression" and similar terms are hedonic terms describing the niceness and conciseness of the odor impression conveyed by aroma chemicals. The more general hedonic terms "advantageous sensory characteristics" or "advantageous organoleptic characteristics" describe the pleasantness and conciseness of the organoleptic impression conveyed by aroma chemicals. The terms "organoleptic" and "sensory" in the context of the present invention relate to olfactory or flavor characteristics. "Pleasantness" and "clarity" are terms well known to those skilled in the art, such as perfumers. Pleasantness generally refers to a pleasant sensory impression that occurs spontaneously and is perceived positively. However, "pleasant" does not necessarily have to be synonymous with "sweet". "Pleasant" could also be the odor of musk or sandalwood. "Clarity" generally refers to a sensory impression that occurs spontaneously and that reproducibly evokes something specific and identical to the same test panel. For example, if a substance has an odor that spontaneously recalls the odor of "apple", then it will have a distinct "apple" odor. If this apple odor is very pleasant, for example because it recalls sweet, ripe apples, then the odor is called "pleasant". On the other hand, a typical tart apple odor may also be distinct. If both reactions occur when smelling the substance, in this example if it smells both pleasantly and distinctly apple-like, then the substance has particularly advantageous sensory properties.

[0030] The term "strong odorant" refers to a substance or aroma chemical that has a strong odor impression. Strong odor impression is understood to mean the property of an aroma chemical that allows it to be perceived intensely even at very low gas space concentrations.

[0031] Its intensity can be measured by determining the threshold value, which no longer needs to be defined, is the exact concentration of a substance at which a representative test panel can still perceive an odor impression in the relevant gas space. Among the known classes of substances, the most intense-smelling ones, i.e. those with a very low odor threshold, are probably the thiols, whose threshold is in the range of ppb / m 3 It is often an area.

[0032] The term "tenacity" describes the evaporation behavior of fragrance chemicals over time. Tenacity can be determined, for example, by applying the fragrance chemical to a test strip and then olfactory evaluation of the odor impression of the test strip. For fragrance chemicals with high tenacity, the period during which the panel can still discern the fragrance impression is long.

[0033] The term "substantivity" describes the interaction of fragrance chemicals with a surface, such as skin or a textile, especially after subsequent treatment of the surface, such as washing. Substantivity can be determined, for example, by washing textiles with a textile detergent composition comprising the fragrance chemicals and then by olfactory evaluation of the textiles immediately after washing (wet textiles) as well as evaluation of the dried textiles after extended storage.

[0034] The term "stability" describes the behavior of a fragrance chemical when in contact with oxygen, light and / or other substances. A highly stable fragrance chemical maintains its fragrance profile, preferably over an extended period of time, in a wide variety of compositions and under a variety of storage conditions.

[0035] Preferably, the retention, substantivity and stability of the fragrance chemicals in the composition should be high in order to impart a long lasting fragrance impression to the composition or to surfaces treated with the composition.

[0036] The terms "booster," "boosting," or "boost" are used herein to describe the effect of enhancing and / or modifying the aroma of an aroma chemical or of a composition. The term "enhancing" includes improving the pleasantness and / or clarity of the aroma and / or improving the intensity. The term "modifying" includes changing the aroma profile.

[0037] The effect of the enhancer is particularly desirable in fragrance compositions where the application requires a top note-characterized odor that is particularly rapid and intensively delivered, for example in deodorants, air fresheners or in the taste area in chewing gum.

[0038] The terms "compound" and "substance" are used interchangeably throughout this invention.

[0039] Composition A comprising compounds (I) and (II) as defined above as components (a) and (b) may be a mixture consisting essentially of compounds (I) and (II) or may be a composition containing further components as defined below, such as solvents or other carriers, aroma chemicals different from (I) and (II), surfactants, etc. "Essentially" means that the mixture may contain traces of impurities, and "trace amounts" means up to 5% by weight, preferably up to 2% by weight, more preferably up to 1% by weight, based on the total weight of said mixture. In the case of using composition A according to the invention as aroma chemicals, as well as in the case of the method of using composition A, composition A is preferably a mixture consisting essentially of compounds (I) and (II) or a mixture consisting essentially of compounds (I) and (II) and a carrier, such as a solvent. The carrier in this case generally has no or weak aroma properties that do not change the aroma properties of the mixture of compounds (I) and (II). More preferably, in the case of the use of composition A according to the present invention as an aroma chemical, as well as in the method of using said composition A, composition A is preferably a mixture consisting essentially of compounds (I) and (II).

[0040] C1-C3 alkyl refers to methyl, ethyl, n-propyl, or isopropyl. C1-C4 alkyl refers to methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl.

[0041] Formyl is a -C(=O)H group.

[0042] C1-C3 alkylcarbonyl is a -C(=O)-R group, where R is a C1-C3 alkyl. Examples are methylcarbonyl (acetyl; -C(=O)-CH3), ethylcarbonyl (propanoyl; -C(=O)-CH2CH3), n-propylcarbonyl (n-butanoyl; -C(=O)-CH2CH2CH3), and isopropylcarbonyl (isobutanoyl; -C(=O)-CH(CH2)3).

[0043] The term "stereoisomers" as used in connection with the present invention specifically relates to geometric or optical isomers, such as enantiomers or diastereomers, the latter existing due to two or more stereocenters in the molecule, (bridged) ring systems or C=C double bonds.

[0044] For purposes of the present invention, stereoisomers of compound (I) may also be characterized as "exo" or "endo" isomers. Exo isomers are those that have the -OR 1 Compound (I) in which the group points in the same direction as the shortest bridge of the bicyclic ring; and wherein the oxygen ring members of the bicyclic ring are referenced to a "plane" formed by the six carbon ring atoms. In the endo isomer, -OR 1 The group points away from the shortest bridge of the bicyclic ring system (ie, towards the oxygen ring member of the bicyclic ring).

[0045] In the context of the present invention, the term "pure enantiomer" is understood as a pure enantiomer in the appropriate sense, i.e. the antipode is below the detection threshold, and also as a non-racemic mixture of a particular compound, in which the particular enantiomer is present in an enantiomeric excess of at least 90% ee, preferably at least 95% ee.

[0046] In the context of the present invention, the term "pure enantiomer" is understood as a pure diastereomer in the appropriate sense, i.e. the other diastereomer is below the detection threshold, and also as a mixture of diastereomers of a particular compound, where the particular diastereomer is present in an amount of at least 90%, preferably at least 95%, relative to the total amount of diastereomers of said compound.

[0047] In the context of the present invention, the terms "Compound I", "Compound (I)" or "compound of formula (I)" refer to the form of the compound as obtained in the non-stereoselective process used for its production, unless defined as a specific stereoisomer or a mixture of specific stereoisomers. However, the term is also used when it is not necessary or possible to specify in more detail the stereochemistry of Compound (I).

[0048] Similarly, the terms "Compound II", "Compound (II)" or "compound of formula (II)", when not defined as a specific stereoisomer or a mixture of specific stereoisomers, refer to the form of the compound as obtained in the non-stereoselective process used for its production. However, the term is also used when it is not necessary or possible to specify the stereochemistry of Compound (II) in more detail.

[0049] If a compound of formula (I) is defined hereinafter as being a specific defined compound (as opposed to a mixture of different compounds I), this means that this compound comprises less than 2% by weight, preferably less than 1% by weight, of further compounds (I) relative to the total weight of the specific defined compound (I) and any further compounds (I) optionally present.

[0050] In mixtures containing different compounds (I), these are R 1 The mixture is composed of 2-hydroxy-1,4-cineole (i.e., compound (I) [wherein R 1 is H] and one or more ethers thereof (i.e., compound (I) [wherein R 1 is C1-C4 alkyl] or one or more esters thereof (i.e., compound (I) [wherein, R 1 is formyl or C1-C3 alkylcarbonyl) or one or more ethers thereof and one or more esters thereof; or the mixture may contain two or more different ethers, or may contain two or more different esters, or may contain one or more ethers and one or more esters. 1 Compound (I) in which R is not hydrogen 1 By the preparation process from compounds (I) where R is hydrogen or from other alcohol precursors which need to be converted to ethers or esters, such compounds may be easily obtained if the reaction is not completed and / or if the isolation / purification step is not performed or is not sufficient. 1 It may also include compounds (I) in which R 1 Compounds (I) in which is H are generally only present in trace amounts, such as up to 10% by weight, preferably up to 5% by weight, in particular up to 2% by weight, based on the total weight of all compounds (I) present in the mixture.

[0051] When compound (I) is not specified to be a specific compound (I) but may be a mixture of different compounds (I), the mixture of stereoisomers of compound (I) may be a mixture of different stereoisomers of a specific compound (I) or a mixture of stereoisomers of different compounds (I).

[0052] The following remarks concerning preferred definitions of the compounds of formulae (I) and (II) (where applicable) as well as other preferred properties of the compositions, uses and methods of the invention are valid on their own as well as in combination with one another.

[0053] Embodiment (Ex) of the present invention General and preferred embodiments Ex are summarized in the following non-exhaustive list: Further preferred embodiments will become apparent from the paragraphs following this list.

[0054] E.1. (a) Formula (I) [ka] [In the formula, R 1 is hydrogen, C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl, or with a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I); (b) Formula (II) [ka] or a mixture of different stereoisomers thereof 2. Use of a composition comprising the compound (composition A) as a fragrance chemical.

[0055] E.2. In the compound of formula (I), R 1 The use according to embodiment E.1, wherein is formyl or C1-C3 alkylcarbonyl.

[0056] E.3. In the compound of formula (I), R 1The use according to embodiment E.2, wherein is C1-C3 alkylcarbonyl.

[0057] E.4. In the compound of formula (I), R 1 The use according to embodiment E.3, wherein is methylcarbonyl or ethylcarbonyl.

[0058] E.5. In the compound of formula (I), R 1 The use according to embodiment E.4, wherein is methylcarbonyl.

[0059] E.6. In the compound of formula (I), R 1 The use according to embodiment E.1, wherein is C1-C4 alkyl.

[0060] E.7. In the compound of formula (I), R 1 The use according to embodiment E.6, wherein is C1-C3 alkyl.

[0061] E.8. In the compound of formula (I), R 1 The use according to embodiment E.7, wherein is methyl or ethyl.

[0062] E.9. In the compound of formula (I), R 1 The use according to embodiment E.8, wherein is ethyl.

[0063] E.10. In the compound of formula (I), R 1 The use according to embodiment E.1, wherein is hydrogen.

[0064] E.11. In the compound of formula (I), -OR 1 The use according to any one of embodiments E.1 to E.10, wherein the group is attached at the exo position.

[0065] E.12. The use according to any one of embodiments E.1 to E.11, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 100:1 to 1:100.

[0066] E.13. The use according to embodiment E.12, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of from 50:1 to 1:50.

[0067] E.14. The use according to embodiment E.13, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 1:1 to 1:50.

[0068] E.15. The use according to embodiment E.14, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of from 1:2 to 1:40.

[0069] E.16. The use according to embodiment E.15, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 1:2 to 1:30.

[0070] E.17. The use according to embodiment E.16, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 1:5 to 1:30.

[0071] E.18. The use according to embodiment E.16, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of from 1:2 to 1:15, or from 1:5 to 1:15.

[0072] E.19. The use according to any one of embodiments E.1 to E.18, wherein the composition is a mixture consisting essentially of compounds (I) and (II) as defined in any one of embodiments E.1 to E.18.

[0073] E.20. Use according to any one of embodiments E.1 to E.19 as a fragrance.

[0074] E.21. Use of a composition according to any one of the embodiments E.1 to E.19 (in particular of a mixture essentially consisting of compounds (I) and (II) according to any one of the embodiments E.1 to E.19) for modifying and / or enhancing the fragrance of a composition.

[0075] E.22. Use according to embodiment E.21 for modifying and / or enhancing the fragrance impression of a composition.

[0076] E.23. The use according to embodiment E.22 for modifying the odor characteristics of a ready-to-use fragrance composition.

[0077] E.24. The composition according to any one of embodiments E.1 to E.19, i.e. (a) a compound of formula (I) according to any one of the embodiments E.1 to E.11 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I), (b) a compound of formula (II) as defined in embodiment E.1 or a stereoisomer thereof or a mixture of different stereoisomers thereof, A composition (composition A).

[0078] E.25. The composition according to embodiment E.24, wherein the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 1:1 to 1:50, in particular 1:2 to 1:30, more particularly 1:2 to 1:15 or 1:5 to 1:30 or 1:5 to 1:15.

[0079] E.26. In the compound of formula (I), R 1 The composition according to embodiment E.24 or E.25, wherein when is hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of from 3:1 to 1:100.

[0080] E.27. In the compound of formula (I), R 1 The composition of embodiment E.26, wherein when is hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of 1:1 to 1:100.

[0081] E.28. In the compound of formula (I), R 1 The composition of embodiment E.27, wherein when is hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of 1:1 to 1:50.

[0082] E.29. In the compound of formula (I), R 1 The composition of embodiment E.28, wherein when is hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of 1:2 to 1:30.

[0083] E.30. In the compound of formula (I), R 1 The composition of embodiment E.29, wherein when is hydrogen, the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 1:2 to 1:15, or 1:5 to 1:30, or 1:5 to 1:15.

[0084] E.31. In the compound of formula (I), R 1 The composition of any one of embodiments E.24 to E.30, wherein when is not hydrogen, the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 100:1 to 1:100.

[0085] E.32. In the compound of formula (I), R 1 The composition of embodiment E.31, wherein when is not hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of from 50:1 to 1:50.

[0086] E.33. In the compound of formula (I), R 1 The composition of embodiment E.32, wherein when is not hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of 1:1 to 1:50.

[0087] E.34. In the compound of formula (I), R 1 The composition of embodiment E.33, wherein when is not hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of 1:2 to 1:30.

[0088] E.35. In the compound of formula (I), R 1 The composition of embodiment E.34, wherein when is not hydrogen, the compound of Formula (I) and the compound of Formula (II) are present in a molar ratio of from 1:2 to 1:15, or from 1:5 to 1:30, or from 1:5 to 1:15.

[0089] E.36. The composition of any one of embodiments E.24 to E.35, further comprising at least one additional ingredient selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants, and deodorant actives.

[0090] E.37. The composition described in embodiment E.36, further comprising at least one additional component selected from the group consisting of fragrance chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants, and deodorant actives.

[0091] E.38. A composition (composition B) comprising a compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as defined in any one of embodiments E.1 to E.11; and at least one further component selected from the group consisting of aroma chemicals, non-aroma chemical carriers, antioxidants, and deodorant actives, different from compound (I) as defined in embodiment E.1 and different from compound (II); R if the composition comprises menthol, 4-hydroxycarbomthone, 3,7-dimethyl-2,6-octadiene, krypton, p-menthane-1,2-diol, toluene, dichloromethane, tetrahydrofuran, dimethylformamide, hexane, or chloroform. 1 is not hydrogen; When the composition contains dichloromethane or hexane, R 1 is not acetyl (methylcarbonyl; -C(O)CH3); R 1 is hydrogen and the aroma chemical different from compound (I) is a compound of formula (II) as defined in claim 1, with the proviso that the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 3:1 to 1:>1, preferably 3:1 to 1:100, more preferably 1:1 to 1:100, even more preferably 1:1 to 1:50, in particular 1:2 to 1:30, more particularly 1:2 to 1:15.

[0092] E.39. The composition of embodiment E.38, wherein at least one further component is selected from the group consisting of fragrance chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants, and deodorant actives.

[0093] E.40. In the compound of formula (I), R 1 The composition according to any one of embodiments E.38 and E.39, wherein is C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl.

[0094] E.41. In the compound of formula (I), R 1 The composition of embodiment E.40, wherein is C1-C4 alkyl or C1-C3 alkylcarbonyl, preferably C1-C3 alkyl or acetyl.

[0095] E.42. In the compound of formula (I), R 1 The composition of embodiment E.41, wherein is C1-C3 alkyl.

[0096] E.43. The composition of any one of embodiments E.36 to E.42, wherein the non-fragrance chemical carrier comprises one or more solvents, which are selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

[0097] E.44. The aroma chemicals different from compounds (I) and (II) are geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, (preferably with a cis content of more than 60% by weight), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl a alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate ester, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, α-ionone, α-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-carboxaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadec-5-enone, (Z)-3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide, 15-pentadeca ... Qu-12-enolide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-Tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably with a cis content of 70% by weight or more), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methyl The composition of any one of embodiments E.36 to E.43, wherein the acetylated pentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2-tert-butylcyclohexyl)acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-n-methylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0098] E.45. The composition of any one of embodiments E.24 to E.44, selected from the group consisting of perfume compositions, body care compositions, oral or dental hygiene products, hygiene products, cleaning compositions, textile detergent compositions, compositions for scent dispensers, food products, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0099] E.46. Use of a compound of formula (I) according to any one of embodiments E.1 to E.11 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as aroma chemicals; preferably of R. jaeschkeana as aroma chemicals in essential oil obtained from the rhizomes of Ferula Jaeschkeana. 1is hydrogen.

[0100] E.47. The use according to embodiment E.46 as a fragrance.

[0101] E.48. Use of a compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) according to any one of embodiments E.1 to E.11 for modifying and / or enhancing the aroma of a composition; for modifying and / or enhancing the aroma of menthol or of an essential oil obtained from the rhizomes of Ferula Jaeschkeana, R 1 is hydrogen.

[0102] E.49. Use according to embodiment E.48 for modifying and / or enhancing the fragrance impression of a composition.

[0103] E.50. The use according to embodiment E.49 for modifying the odor characteristics of a ready-to-use fragrance composition.

[0104] E.51.R 1 The use according to any one of embodiments E.46 to E.50, wherein is C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl.

[0105] E.52.R 1 The use according to embodiment E.51, wherein is C1-C3 alkyl.

[0106] E.53. Formula (I) [ka] [In the formula, R 1 is C1-C3 alkyl, formyl, or ethylcarbonyl; or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I).

[0107] E.54.R 1 The use according to embodiment E.53, wherein is C1-C3 alkyl, or ethylcarbonyl.

[0108] E.55.R 1 The use according to embodiment E.54, wherein is methyl, ethyl, or ethylcarbonyl.

[0109] E.56.R 1 The use according to embodiment E.55, wherein is ethyl.

[0110] Companies from which the aromachemical compounds identified by the trade names and suffixes listed above are available are listed below.

[0111] Composition A and its use In a preferred embodiment, in the compound of formula (I), R 1 is formyl or C1-C3 alkylcarbonyl, more preferably C1-C3 alkylcarbonyl, particularly methylcarbonyl (acetyl) or ethylcarbonyl (propionyl), specifically methylcarbonyl.

[0112] In another preferred embodiment, in the compound of formula (I), R 1 is C1 to C4 alkyl, more preferably C1 to C3 alkyl, particularly methyl or ethyl, specifically ethyl.

[0113] In another preferred embodiment, in the compound of formula (I), R 1 is hydrogen.

[0114] In the compound of formula (I), -OR 1 The group can be attached at the exo or endo position.

[0115] In this case, the exo position is OR 1This means that the bond between a carbon ring atom and the oxygen atom of the group points in the same direction as the oxygen ring member of the bicycle, relative to the plane formed by the six carbon ring atoms.

[0116] In this case, the end position is OR 1 This means that the bond between a carbon ring atom and the oxygen atom of the group points away from the oxygen ring member of the bicycle, relative to the plane formed by the six carbon ring atoms.

[0117] In a preferred embodiment, in the compound of formula (I), -OR 1 The group is attached at the exo position.

[0118] Preferably, the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 100:1 to 1:100, more preferably 50:1 to 1:50, even more preferably 1:1 to 1:50, particularly preferably 1:2 to 1:40, in particular 1:2 to 1:30, for example 1:2 to 1:15 or 1:5 to 1:30 or especially 1:5 to 1:15.

[0119] However, when composition A itself is concerned (and not its use or its method of use according to the invention), the above molar ratios are preferably such that in compound (I) R 1 Applies only if R is not hydrogen. 1 When is hydrogen, the compound of formula (I) and the compound of formula (II) are preferably present in a molar ratio of from 3:1 to 1:100, more preferably from 1:1 to 1:100, even more preferably from 1:1 to 1:50, in particular from 1:2 to 1:30, more particularly from 1:2 to 1:15 or from 1:5 to 1:30, or especially from 1:5 to 1:15.

[0120] In an embodiment of the present invention, the composition comprising compounds (I) and (II) is a mixture consisting essentially of compounds (I) and (II). As explained above, "essentially" means that the mixture may contain trace amounts of impurities, and "trace amounts" means up to 5% by weight, preferably up to 2% by weight, more preferably up to 1% by weight, based on the total weight of the mixture.

[0121] In another embodiment, the composition A comprising compounds (I) and (II) further comprises a component different from compounds (I) and (II).Preferably, in this case, the composition further comprises at least one further component selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants, and deodorant actives; in particular from the group consisting of fragrance chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants, and deodorant actives.Suitable and preferred fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, surfactants, oil components, solvents, antioxidants, and deodorant actives are defined below.

[0122] R 1 Compounds (I) and (II) where is hydrogen are known materials and are either commercially available or can be prepared by standard procedures.

[0123] Preferably, R 1 Compound (I), where R is hydrogen, is obtained from renewable sources, more precisely from terpinen-4-ol (3), which is epoxidized at the double bond to the epoxide compound (1). By acid-catalyzed rearrangement, R 1 is obtained (referred to as (I') in the scheme below): [ka]

[0124] This synthetic route is described in WO 2018 / 210662, EP 0081892, or EP 0081893, and the documents cited therein. Terpinen-4-ol (3) can be isolated from natural sources and is available as a racemate or a non-racemic mixture in which one of the two enantiomers predominates. The stereoinformation of 3 is also present in (I') since the two steps proceed stereoselectively under the reaction conditions described in WO 2018 / 210662, EP 0081892, or EP 0081893. Alternatively or additionally, compounds 3, 1, or (I') can be subjected to enantiomeric resolution to obtain high enantiomeric purity. Suitable methods are known in the art, for example the method described in WO 2018 / 210662, which involves selective enzyme-catalyzed acylation of only one of the enantiomers and separation from the non-acylated antipodes.

[0125] Compound (I) [wherein, R 1 is C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl] can be prepared by standard procedures, for example by converting compound (I) [wherein R 1 is hydrogen] by etherification (R 1 to obtain a compound in which R is C1-C4 alkyl) or by esterification (R 1 is formyl or C1-C3 alkylcarbonyl).

[0126] Ester compound (I) [wherein R 1 is formyl or C1-C3 alkylcarbonyl] is reacted with compound (I) [wherein R is a carboxylic acid] under typical esterification conditions, optionally with removal of the reaction water (when the acid itself is used) or the acid (when the anhydride is used) generated to increase the reaction rate, or under neutralization (when the acid halide is used), to form 1is hydrogen], i.e., formic acid, acetic acid, propionic acid, butyric acid, or isobutyric acid, or a more active derivative of the above acids, such as the acid halides (e.g., chlorides or bromides), anhydrides, or esters thereof with active esters.

[0127] The esterification can be carried out in the presence of an esterification catalyst; this is particularly indicated when using the carboxylic acid itself. Suitable esterification catalysts are well known in the art, for example, metal-based catalysts, such as iron, cadmium, cobalt, lead, zinc, antimony, magnesium, titanium and tin catalysts in the form of metals, metal oxides or metal salts, such as metal alkoxylates; or acids, such as mineral acids, such as sulfuric acid, hydrochloric acid or phosphoric acid; organic sulfonic acids, such as methanesulfonic acid or paratoluenesulfonic acid, or strong acid cation exchange resins.

[0128] The term "strongly acidic cation exchanger" refers to a cation exchanger in the H+ form that has strongly acidic groups. The strongly acidic groups are generally sulfonic acid groups; they are generally attached to a polymer matrix that may be gel-like and / or macroporous. Styrene (co)polymers containing sulfonic acid groups are preferred, in particular styrene-divinylbenzene copolymers containing sulfonic acid groups. Commercially available examples of such cation exchangers are Lewatit® (Lanxess), Purolite® (The Purolite Company), Dowex® (Dow Chemical Company), Amberlite® (Rohm and Haas Company), Amberlyst® (Rohm and Haas Company). Preferred strongly acidic cation exchangers are: Lewatit® K 1221, Lewatit® K 1461, Lewatit® K 2431, Lewatit® K 2620, Lewatit® K 2621, Lewatit® K 2629, Lewatit® K 2649, Amberlite® FPC 22, Amberlite® FPC 23, Amberlite® IR. 120, Amberlyst® 131, Amberlyst® 15, Amberlyst® 31, Amberlyst® 35, Amberlyst® 36, Amberlyst® 39, Amberlyst® 46, Amberlyst® 70, Purolite® SGC650, Purolite® C100H, Purolite® C150H, Dowex® 50X8, Serdolit® red and Nafion® NR-50. Alternatively, the cation exchanger can be a perfluorinated ion exchange resin, for example, sold under the Nafion® brand by DuPont.

[0129] The esterification can also be carried out in the presence of a base; this is particularly indicated when using carboxylic acid halides. Suitable bases are, for example, tertiary amines such as trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine, etc. or basic N-heterocyclic compounds such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN, and other organic bases.

[0130] The reaction can be carried out in a solvent or without a solvent. Suitable solvents are, for example, alkanes such as hexane or heptane, halogenated C1-C4 alkanes such as dichloromethane, chloroform, or dichloroethane, cycloalkanes such as cyclohexane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, or dichlorobenzene, aliphatic ethers such as diisopropyl ether or methyl-tert-butyl ether, or cyclic ethers such as tetrahydrofuran or dioxane. Certain solvents can be used alone or in the form of mixtures with one another.

[0131] After completion of the reaction, if necessary after neutralization (especially if an acid halide or anhydride was used as starting material or if an excess of acid was used) and / or after removal of the catalyst (especially if it is a solid, such as one of the metal-based catalysts or ion exchange resins mentioned above), the esterification product can be isolated by conventional means, for example by distillation, extraction or chromatographic methods. If desired, the isolated product can then be further purified.

[0132] Ether compound (I) [wherein R 1 is C1-C4 alkyl] is typically reacted with compound (I) [wherein R 1 is hydrogen] to alkylating reagent R 1 -X[wherein, R 1is a C1-C4 alkyl and X is a leaving group such as a halogen atom, e.g., Cl, Br, or I, or a sulfonate group, e.g., tosylate, mesylate, triflate, or nonaflate.

[0133] Suitable bases can be selected from inorganic bases and organic bases.Suitable inorganic bases are, for example, alkali metal carbonates, such as Li2CO3, Na2CO3, K2CO3 or Cs2CO3, alkali metal hydroxides, such as LiOH, NaOH or KOH, and hydride donors, such as NaH, LiAlH4 or NaBH4.Examples of suitable organic bases correspond to those listed above, i.e. organic bases such as tertiary amines, such as trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine, etc., or basic N-heterocyclic compounds, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.

[0134] The alkylation reaction is carried out under conventional alkylation reaction conditions well known to those skilled in the art.

[0135] The reaction can be carried out in a solvent or without a solvent. Examples of suitable solvents are listed above for the ester reaction.

[0136] After completion of the reaction, the etherified product, optionally after neutralization (particularly when X is a halogen atom or when acidic conditions are applied), can be isolated by conventional means, such as distillation, extraction or chromatographic techniques. If desired, the isolated product can then be further purified.

[0137] Compound (II) (the carbenone) is commercially available.

[0138] The composition containing the compounds (I) and (II) can be obtained by simply mixing the compounds (I) and (II) in a desired mixing ratio. Alternatively, the compound (II) can be added to the compound (I) [wherein R 1 is hydrogen] and compound (II) are used as starting materials in an esterification or etherification reaction.

[0139] The present invention further relates to the use of composition A as defined above comprising compounds (I) and (II) as an aroma chemical; in particular as a fragrance, in particular in the form of a mixture consisting essentially of compounds (I) and (II).

[0140] Specifically, carbenoside (II) and 2-hydroxy-1,4-cineole (R 1 A composition containing compound (I) where =H in an approximate weight ratio of 87:12 is used to impart one of the following olfactory notes: caraway, terpenic, spicy, woody.

[0141] Specifically, carbenoside (II) and 2-hydroxy-1,4-cineole (R 1 Compositions containing 2-hydroxy-1,4-cinerol (compound (I)) in a weight ratio of 99:1 to 1:99 are used to impart one of the above olfactory notes, with increasing amounts of 2-hydroxy-1,4-cinerol resulting in a milder scent; 25:75 to 1:99 results in a less spicy and more fruity impression.

[0142] Specifically, carbenoside (II) and acetate of 2-hydroxy-1,4-cineole (R 1 A composition containing compound (I) where =-C(O)CH3 in an approximate weight ratio of 87:12 is used to impart one of the following olfactory notes: powdery, caraway, woody.

[0143] Specifically, carbenoside (II) and acetate of 2-hydroxy-1,4-cineole (R 1 Compositions containing compound (I) (=-C(O)CH3) in a weight ratio of 99:1 to 1:99 are used to impart one of the above olfactory notes, with increasing amounts of (4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-yl)acetate resulting in a milder scent; with a ratio of 25:75 to 1:99 the scent becomes less spicy and more fruity.

[0144] Specifically, carbenoside (II) and the ethyl ether of 2-hydroxy-1,4-cineole (R 1 A composition containing compound (I) (=CH2CH3) in a weight ratio of approximately 87:12 is used to impart one of the following olfactory notes: powdery, citrus and caraway with a fruity side.

[0145] Specifically, carbenoside (II) and the ethyl ether of 2-hydroxy-1,4-cineole (R 1 A composition containing 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (compound (I) =CH2CH3) in a weight ratio of 99:1 to 1:99 is used to impart one of the above olfactory notes, with increasing amounts of 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane resulting in a milder scent. At 50:50 to 1:99, the spiciness is reduced and the impression is more citrus and fruity.

[0146] In addition to their olfactory properties, compounds (I) and (II) exhibit advantageous secondary properties.

[0147] For example, they can impart a better sensory profile as a result of synergistic interaction with other fragrances, meaning that they have the effect of enhancing other fragrances (they give "volume" to the composition; they act as "lifters"), and therefore are suitable as enhancers of other fragrances.

[0148] The present invention also relates to the use of composition A as defined above, comprising compounds (I) and (II), in particular in the form of a mixture essentially consisting of compounds (I) and (II), for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition, and in particular as an enhancer of other fragrances.

[0149] By enhancer effect is meant that in perfume formulations, the substance improves and intensifies the overall impression of the mixture. For example, in the mint field, menthyl methyl ether is known to enhance the aroma chemicals or taste mixture of peppermint oil, particularly significantly strengthening the top note and resulting in a more complex perception, even though this ether does not have a particularly strong odor by itself. In fragrance applications, Hedione® (methyl dihydrojasmonate) by itself only exhibits a light jasmine flower note, but as an odor enhancer, it enhances the diffusion, freshness and richness of the volume of the perfume composition. The enhancer effect is particularly desired when applications characterized by a top note are required, such as in deodorants, air fresheners, or in the taste area in chewing gum, where the odor is delivered particularly quickly and intensively.

[0150] To obtain such an enhancing effect, compounds (I) and (II) are generally used in an amount of 0.1 to 20% by weight, preferably in an amount of 0.5 to 5% by weight, in particular in a total amount of 0.6 to 3% by weight, based on the total weight of the fragrance mixture.

[0151] Additionally, compounds (I) and (II) may provide additional positive effects to the compositions in which they are used, for example, they may enhance the overall performance of the composition in which they are incorporated, such as the stability (e.g., formulation stability), extendibility or durability of the composition.

[0152] A further embodiment of the present invention relates to a method for preparing an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, comprising incorporating compounds (I) and (II) into a composition of interest, such as a ready-to-use composition, thereby obtaining an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition. Alternatively, the present invention relates to a method for preparing an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, comprising mixing compounds (I) and (II) with at least one aroma chemical different from compounds (I) and (II), and / or at least one non-aroma chemical carrier, and / or at least one antioxidant, and / or at least one deodorant active. Suitable and preferred aroma chemicals different from compounds (I) and (II), non-aroma chemical carrier, antioxidant and deodorant active are described below.

[0153] For example, the method can be carried out by mixing compounds (I) and (II) as defined above with at least one further ingredient selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants and deodorant actives.

[0154] The present invention also relates to a method for modifying the odor characteristics of an aroma chemical composition, particularly a fragrance composition, especially a ready-to-use fragrance composition, which comprises incorporating compounds (I) and (II) into the aroma chemical composition, particularly a fragrance composition, especially a ready-to-use fragrance composition.

[0155] The present invention further relates to a method for imparting a fragrance, preferably a fragrance, to a composition, in particular to an (other) ready-to-use composition, which comprises incorporating compounds (I) and (II) into the composition to be aromatized, in particular to be fragranced.

[0156] In a particular embodiment, the present invention relates to a method for imparting one of the following olfactory notes: caraway, terpenic, spicy, woody; or any combination thereof to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method for the preparation of a composition comprising: compound (I) (wherein: =H) in a weight ratio of approximately 87:12 in a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition, or a crop protection composition.

[0157] In another embodiment, the present invention relates to a method for imparting one of the above olfactory notes, or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method for the preparation of a composition comprising a compound (I) (wherein: =H) in a weight ratio of 99:1 to 1:99 in a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition, or a crop protection composition. Increasing the amount of 2-hydroxy-1,4-cineole results in a milder fragrance. At a ratio of 25:75 to 1:99, the spiciness is reduced and a more fruity impression is obtained.

[0158] In another particular embodiment, the present invention relates to a method for imparting one of the following olfactory notes: powdery, caraway, woody; or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method of treating a disease comprising the step of incorporating a composition comprising compound (I) (wherein compound (I) is =-C(O)CH3) in a weight ratio of approximately 87:12 into a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0159] In another particular embodiment, the present invention relates to a method for imparting one of the above olfactory notes, or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method for the preparation of a composition containing a compound (I)) having a weight ratio of 99:1 to 1:99 in a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food, a dietary supplement, a pharmaceutical composition, or a crop protection composition. Increasing the amount of (4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-yl)acetate results in a milder scent. At a ratio of 25:75 to 1:99, the spiciness is reduced and the impression is more fruity.

[0160] In another particular embodiment, the present invention relates to a method for imparting one of the following olfactory notes: caraway with a powdery, citrus and fruity profile; or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method of treating a disease comprising the step of incorporating a composition comprising compound (I) (wherein: =CH2CH3) in a weight ratio of approximately 87:12 into a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0161] In another particular embodiment, the present invention relates to a method for imparting one of the above olfactory notes, or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method for the preparation of a composition comprising a compound (I) (=CH2CH3) in a weight ratio of approximately 87:12 in a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food, a dietary supplement, a pharmaceutical composition, or a crop protection composition. The amount of 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane is increased to make the scent milder. At a ratio of 50:50 to 1:99, the spiciness is reduced, and the impression is more citrus and fruity.

[0162] Composition B The present invention further relates to a composition B comprising a compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as defined above, and at least one further component selected from the group consisting of aroma chemicals different from compounds (I) and (II), non-aroma chemical carriers, antioxidants and deodorant actives; in particular from the group consisting of aroma chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants and deodorant actives, Preferably, when the composition comprises menthol, 4-hydroxycarbomethane, 3,7-dimethyl-2,6-octadiene, krypton, p-menthane-1,2-diol, toluene, dichloromethane, tetrahydrofuran, dimethylformamide, hexane, or chloroform, R 1 is not hydrogen; if the composition contains dichloromethane or hexane, R 1 is not acetyl (methylcarbonyl; -C(O)CH3), and R 1 is hydrogen and the aroma chemical different from compound (I) is a compound of formula (II) as defined in claim 1, with the proviso that the compound of formula (I) and the compound of formula (II) are present in a molar ratio of 3:1 to 1:>1, preferably 3:1 to 1:100, more preferably 1:1 to 1:100, even more preferably 1:1 to 1:50, in particular 1:2 to 1:30, more particularly 1:2 to 1:15.

[0163] Composition B differs from composition A in that the presence of compound (II) is not essential, but the presence of at least one of the further components identified above is essential.

[0164] In composition B, in the compound of formula (I), R 1 is preferably C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl, more preferably C1-C4 alkyl or C1-C3 alkylcarbonyl, even more preferably C1-C3 alkyl, in particular ethyl or methyl, specifically ethyl.

[0165] As already described with respect to composition A, in a preferred embodiment, in the compound of formula (I), -OR 1 The group is preferably attached at the exo position.

[0166] Compound (I) can be prepared as described above for Composition A.

[0167] Suitable fragrance chemicals, non-fragrance chemical carriers, surfactants, oil components, solvents, antioxidants, and deodorant actives that are different from compounds (I) and (II) are listed below.

[0168] Preferably, when the non-fragrance chemical carrier in Composition B comprises one or more solvents, these are selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

[0169] The present invention further relates to the use of a compound of formula (I) as defined above or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as aroma chemicals, in particular as fragrances; preferably as aroma chemicals in the essential oil obtained from the rhizomes of Ferula Jaeschkeana, 1 In this context, R does not include the use of compounds of formula (I) in which R 1 is preferably C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl, more preferably C1-C4 alkyl or C1-C3 alkylcarbonyl, even more preferably C1-C3 alkyl, in particular methyl or ethyl, specifically ethyl.

[0170] Specifically, 2-hydroxy-1,4-cineole acetate (R 1 = Compound (I), -C(O)CH3, is used to impart one of the following olfactory notes: ambrinol, animalic, civety, soft.

[0171] Specifically, the ethyl ether of 2-hydroxy-1,4-cineole (R 1 Compound (I) where =CH2CH3 is used to impart one of the following olfactory notes: herbal, incense.

[0172] In addition to their olfactory properties, compounds (I) exhibit advantageous secondary properties.

[0173] For example, they can impart a better sensory profile as a result of synergistic interaction with other fragrances, meaning that they have the effect of enhancing other fragrances (they give "volume" to the composition; they act as "lifters"), and therefore are suitable as enhancers of other fragrances.

[0174] The present invention also relates to the use of a compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined above for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition, and in particular for use as enhancer of other fragrances. Preferably, the use is of R for modifying and / or enhancing the aroma of menthol or of an essential oil obtained from the rhizomes of Ferula Jaeschkeana. 1 This does not include the use of compounds of formula (I) in which R 1 is preferably C1-C4 alkyl, formyl, or C1-C3 alkylcarbonyl, more preferably C1-C4 alkyl or C1-C3 alkylcarbonyl, even more preferably C1-C3 alkyl, in particular methyl or ethyl, specifically ethyl.

[0175] By enhancer effect is meant that in perfume formulations, the substance improves and intensifies the overall impression of the mixture. For example, in the mint field, menthyl methyl ether is known to enhance the aroma chemicals or taste mixture of peppermint oil, particularly significantly strengthening the top note and resulting in a more complex perception, even though this ether does not have a particularly strong odor by itself. In fragrance applications, Hedione® (methyl dihydrojasmonate) by itself only exhibits a light jasmine flower note, but as an odor enhancer, it enhances the diffusion, freshness and richness of the volume of the perfume composition. The enhancer effect is particularly desired when applications characterized by a top note are required, such as in deodorants, air fresheners, or in the taste area in chewing gum, where the odor is delivered particularly quickly and intensively.

[0176] To obtain such an enhancing effect, compound (I) is generally used in an amount of 0.1 to 20% by weight, preferably in an amount of 0.5 to 5% by weight, in particular in a total amount of 0.6 to 3% by weight, based on the total weight of the fragrance mixture.

[0177] Furthermore, the compounds (I) may provide further positive effects to the compositions in which they are used, for example, they may improve the overall performance of the composition in which they are incorporated, for example the stability, such as the formulation stability, diffusion or residual activity of the composition.

[0178] A further embodiment of the present invention relates to a method for the preparation of an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, which comprises incorporating compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) into a composition of interest, such as a ready-to-use composition, thereby obtaining an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition. Alternatively, the present invention relates to a method for the preparation of an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, which comprises mixing compound (I) or a mixture of different stereoisomers thereof or a mixture of different compounds (I) with at least one aroma chemical different from compounds (I) and (II), and / or at least one non-aroma chemical carrier, and / or at least one antioxidant, and / or at least one deodorant active. Suitable and preferred aroma chemicals different from compounds (I) and (II), non-aroma chemical carrier, antioxidant and deodorant active are described below.

[0179] For example, the method can be carried out by mixing compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as defined above with at least one further ingredient selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants and deodorant actives.

[0180] The present invention also relates to a method for modifying the odor characteristics of an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition, which method comprises incorporating compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) into an aroma chemical composition, in particular a fragrance composition, especially a ready-to-use fragrance composition.

[0181] The present invention further relates to a method for imparting an aroma, preferably a fragrance, to a composition, in particular to an (other) ready-to-use composition, which comprises incorporating compound (I) or a mixture of different compounds (I), or a stereoisomer of one of these compounds (I), or a mixture of one or more stereoisomers of these compounds (I), into the composition to be aromatized, in particular to be fragranced.

[0182] In a particular embodiment, the present invention relates to a method for imparting one of the following olfactory notes: ambrinol, animalic, civet, soft; or any combination thereof, to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the step of: 1 The present invention relates to a method of treating a disease comprising the step of incorporating a compound (I) having the formula: =-C(O)CH3 into a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0183] In another particular embodiment, the present invention relates to a method for imparting one of the following olfactory notes: herbal, incense; or any combination thereof to a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising the steps of: 1 The present invention relates to a method comprising incorporating compound (I) where =CH2CH3 into a perfume composition, a body care composition, an oral and dental hygiene product, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0184] Further general and preferred features of compositions A and B Composition A is optional, and composition B is mandatory, and comprises at least one further component selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants, and deodorant actives. In the case of composition B, when the composition contains menthol, R 1 is not hydrogen.

[0185] The non-fragrance chemical carriers, antioxidants and deodorant actives are, of course, also different from compounds (I) and (II).

[0186] The non-fragrance chemical carrier is in particular selected from the group consisting of surfactants, oil components (emollients) and solvents.

[0187] Thus, in a preferred embodiment, the at least one further component is selected from the group consisting of fragrance chemicals different from compounds (I) and (II), surfactants, oil components (emollients), solvents, antioxidants, and deodorant actives.

[0188] Compound (I) [and in the case of Composition A, compound (II)] has a pleasant odor, low volatility and very high solubility, making it a suitable component of compositions in which a pleasant odor is desired.

[0189] Thus, composition A (if it is not a mixture consisting essentially of (I) and (II)) and composition B are preferably aromachemical compositions, more preferably odorous compositions, especially fragrance compositions.

[0190] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined above (and in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) and at least one further component selected from the group consisting of oil components, solvents, antioxidants and deodorant actives.

[0191] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and in the case of composition A additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one aroma chemical.

[0192] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and in the case of composition A additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one non-aroma chemical carrier.

[0193] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one surfactant.

[0194] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above, and at least one oil component.

[0195] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one solvent.

[0196] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above, and at least one antioxidant.

[0197] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined above (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) and at least one deodorant active.

[0198] Compound (I) [in the case of composition A, mixed with compound (II)] can preferably be used in an aroma composition. In a preferred embodiment, the aroma composition is an odor composition, i.e. a composition which induces an odor impression, in particular a fragrance composition, i.e. a composition which induces a pleasant odor.

[0199] Compositions A (if it is not a mixture consisting essentially of compounds (I) and (II)) and B may be selected from the group consisting of, but not limited to, perfume compositions, body care compositions (including cosmetic compositions), oral and dental hygiene compositions, hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, fragrance dispenser compositions, food products, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0200] Aroma chemicals [different from compounds (I) and (II)] Due to the physical properties of compound (I) (and compound (II) in the case of composition A), the combination of said compounds exhibits substantially versatile solvent properties, particularly good among them as a solvent for aroma chemicals and other ingredients commonly used in scent compositions, such as aroma chemicals, especially fragrance compositions. Thus, compound (I) (and compound (II) in the case of composition A) can be successfully combined with aroma chemicals different from compounds (I) and (II), which allows in particular the creation of aroma compositions (preferably fragrance compositions) with novel and advantageous sensory profiles. In particular, as already explained above, such combinations allow the sensory profile of aroma chemicals (such as fragrances) different from compounds (I) and (II) to be enhanced.

[0201] Compositions A and B may contain at least one fragrance chemical different from compounds (I) and (II). The at least one fragrance chemical may be, for example, 1, 2, 3, 4, 5, 6, 7, 8 or more fragrance chemicals selected from the group consisting of: geranyl acetate (3,7-dimethyl-2,6-octadien-1yl acetate), α-hexyl cinnamaldehyde, 2-phenoxyethyl isobutyrate (Phenirat 1 ), dihydromyrcenol (2,6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably with a cis content of more than 60% by weight) (Hedione 9 , Hedione HC 9 ), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran (Galaxolid 3 ), Tetrahydrolinalool (3,7-dimethyloctan-3-ol), Ethyl linalool, Benzyl salicylate, 2-Methyl-3-(4-tert-butylphenyl)propanal (Lysmeral 2), cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate (Herbaflorat 1 ), citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate (1-phenylethyl acetate), octahydro-2,3,8,8-tetramethyl-2-acetonaphthone and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene (Iso E Super 3 ), Hexyl Salicylate, 4-tert-Butylcyclohexyl Acetate (Oryclone 1 ), 2-tert-butylcyclohexyl acetate (Agrumex HC 1 ), α-ionone (4-(2,2,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one), n-α-methyl ionone, α-isomethyl ionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene carboxaldehyde (Lyral 3 ), α-amylcinnamaldehyde, ethylene brassylate, (E)- and / or (Z)-3-methylcyclopentadec-5-enone (Muscenon 9 ), 15-pentadec-11-enolide and / or 15-pentadec-12-enolide (Globalide 1 ), 15-Cyclopentadecanolide (Macrolide 1 ), 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone (Tonalid 10 ), 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Floro 9 ), 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol (Sandolen 1), cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde (Vertocitral 1 ), 2,4,4,7-tetramethyloct-6-en-3-one (Claritone 1 ), 2,6-Dimethyl-5-hepten-1-al (Melonal 2 ), borneol, 3-(3-isopropylphenyl)butanal (Florhydral 2 ), 2-methyl-3-(3,4-methylenedioxyphenyl)propanal (Helional 3 ), 3-(4-ethylphenyl)-2,2-dimethylpropanal (Florazon 1 ), 7-methyl-2H-1,5-benzodioxepin-3(4H)-one (Calone), 3,3,5-trimethylcyclohexyl acetate (preferably with a cis content of 70% by weight or more), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol (Ambrinol S 1 ), 3-(4-tert-butylphenyl)-propanal (Bourgeonal 4 ), Ethyl 2-methylpentanoate (Manzanate 4 ), ethoxymethoxycyclododecane (Amberwood 1 ), 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin (Magnolan 1 ), (2-tert-butylcyclohexyl) acetate (Verdox 3 ) and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol (Sandela 4 Therefore, in the context of the present invention, the above mentioned aroma chemicals are preferably combined with a compound of formula (I) as mentioned above or with a mixture of different compounds of formula (I).

[0202] For sources of the products mentioned above, please see below: 1 Product name of Symrise GmbH, Germany; 2 Trade names of BASF SE; 3 Trade name of International Flavors & Fragrances Inc., USA; 4 Givaudan AG,Switzerland; 9 Trade name of Firmenich SA, Switzerland; 10 PFW Aroma chemicals BV, the Netherlands, product name.

[0203] A preferred embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined above (and in the case of composition A additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) and at least one aroma chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and linalool.

[0204] A further embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as defined above (and in the case of composition A, further compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof) and 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol.

[0205] A further embodiment of the invention relates to a composition comprising a compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined (and in the case of composition A additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) and methyl benzoate.

[0206] A preferred embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) as defined above [and in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers] and at least one aroma chemical selected from the group consisting of ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0207] Further fragrance chemicals which may be combined with compound (I) [in the case of composition A, mixed with compound (II)] to form the compositions according to the invention can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published or in K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th Ed., Wiley- VCH, Weinheim 2001. In particular, the following may be mentioned: Extracts from natural sources, such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, e.g. Ambergris Tincture, Amyris Oil, Angelica Seed Oil, Angelica Root Oil, Anise Oil, Valerian Oil, Basil Oil, Tree Moss Absolute, Bay Oil, Wormwood Oil, Benzoin Resin, Bergamot Oil, Beeswax Absolute, Birch Tar Oil, Bitter Almond Oil, Savory Oil, Butu Leaf Oil, Cabreva Oil, Cade Oil, Calmus Oil, Camphor Oil, Cananga Oil, Cardamom Oil, Cascarilla Oil, Cassia Oil, Cassia Absolute, Castorium 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, Dill Weed Oil, Dill Seed Oil, Eau de brouts absolute, oakmoss absolute, elemi oil, tarragon oil, eucalyptus citriodora oil, eucalyptus oil, fennel oil, pine needle oil, galbanum oil, galbanum resin, geranium oil, grapefruit oil, guaiacwood oil, gurjan balsam, gurjan balsam oil, helichrysum absolute, helichrysum oil, ginger oil, iris root absolute, iris root oil, jasmine absolute, chamus oil, chamomile oil blue, roman chamomile oil, carrot seed oil, cascarilla oil, pine needle oil, spearmint oil, caraway oil, labdanum Oil, Labdanum Absolute, Labdanum Resin, Lavandin Absolute, Lavandin Oil, Lavender Absolute, Lavender Oil, Lemongrass Oil, Lovage Oil, Distilled Lime Oil, Pressed Lime Oil, Linalool Oil, Litsea Cucumber Oil, Bay Leaf Oil, Mace Oil, Marjoram Oil, Mandarin Oil, Massoia Bark Oil, Mimosa Absolute, Musk Seed Oil, Mus Tinker, Clary Sage Oil, Nutmeg Oil, Myrrh Absolute, Myrrh Oil, Myrrh Oil, Myrtle Oil, Clove Leaf Oil, Clove Flower Oil, Neroli Oil, Olibanum Absolute, Olibanum Oil, Opopanax Oil,Orange Blossom Absolute, Orange Oil, Origanum Oil, Palmarosa Oil, Patchouli Oil, Parilla Oil, Balsam of Peru Oil, Parsley Leaf Oil, Parsley Seed Oil, Petitgrain Oil, Peppermint Oil, Pepper Oil, Pimento Oil, Pine Oil, Pennyroyal Oil, Rose Absolute, Rosewood Oil, Rose Oil, Rosemary Oil, Dalmatian Sage Oil, Spanish Sage Oil, Sandalwood Oil, Celery Seed Oil, Spike Lavender Oil, Sta - 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 wreath oil, absinthe oil, wintergreen oil, hyssop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil and fractions or components isolated therefrom; Individual aroma 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, etc.; aliphatic alcohols, such as hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, (E)-2-hexenol, (E)- and (Z)-3-hexenol, 1 octen-3-ol, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc.; Aliphatic aldehydes and their acetals, such as hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, 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; hexene, heptanal diethyl acetal, 1,1-dimethoxy-2,2,5-trimethyl-4-hexene, citronellyloxyacetaldehyde, (E / Z)-1-(1-methoxypropoxy)-hex-3-ene, etc.; 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, etc.; Sulfur-containing aliphatic compounds, such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, 1-menthene-8-thiol, etc.; Aliphatic nitriles, such as 2-nonenenitrile, 2-undecenenitrile, 2-tridecenenitrile, 3,12-tridecadienenitrile, 3,7-dimethyl-2,6-octadienenitrile, 3,7-dimethyl-6-octenenitrile, etc.; Esters of aliphatic carboxylic acids, for example (E) and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, hexyl 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-octynate, methyl 2-nonynate, allyl 2-isoamyloxyacetate, methyl-3,7-dimethyl-2,6-octadienoate, 4-methyl-2-pentyl crotonate, and the like; Acyclic terpene alcohols, such as geraniol, nerol, linalool, lavandulol, nerolidol, farnesol, tetrahydrolinalool, 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, -ol, 3,7-dimethyl-4,6-octadien-3-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, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates; Acyclic terpene aldehydes and ketones, such as geranial, neral, citronellal, 7-hydroxy-3,7-dimethyloctanal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranylacetone and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal; cyclic terpene alcohols, such as menthol, isopulegol, α-terpineol. linalool oxide, nopol, cedrol, ambrinol, vetiverol, guajol and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates, and the like; Cyclic terpene aldehydes and ketones, for example, menthone, isomenthone, 8-mercaptomenthan-3-one, carvone, camphor, fenchone, α-ionone, β-ionone, α-n-methylionone, β-n-methylionone, α-isomethylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, γ-damascone, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)- 2-Buten-1-one, 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, nootkatone, dihydronootkatone, 4,6,8-megastigmatrien-3-one, α-sinensal, β-sinensal, acetylated cedarwood oil (methyl cedryl ketone), etc; 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, etc.; Alicyclic 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, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl)pentan-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, etc.; Cyclic and alicyclic ethers, such as cineol, 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-trimethyldodecahydro-naphtho[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, and the like; 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, 7-cyclohexadecen-1-one, (7 / 8)-cyclohexadecen-1-one, 9-cycloheptadecen-1-one, cyclopentadecanone, cyclohexadecanone, etc.; Alicyclic aldehydes, such as 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde, and the like; Alicyclic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one, 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone, methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone, tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl)ketone, etc.; 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 or 6-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate, 4,7-methanooctahydro-5 or 6-indenyl acetate, etc.; Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate; Esters of alicyclic carboxylic acids, such as allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis- and trans-methyl dihydrojasmonate, cis- and trans-methyl jasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, ethyl 2-methyl-1,3-dioxolane-2-acetate, and the like; Aromatic aliphatic alcohols, such as benzyl alcohol, 1-phenylethyl alcohol, 2-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, etc.; 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, etc.; Aromatic aliphatic ethers, such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine, etc.; Aromatic and araliphatic 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-tert-butylphenyl)propanal, 2-methyl-3-(4-isobutylphenyl)propanal, 3-(4-tert-butylphenyl)propanal; cinnamaldehyde, α-butylcinnamaldehyde, α-amylcinnamaldehyde, 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, etc.; 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-benzofuranyl-ethanone, (3-methyl-2-benzofuranyl)ethanone, benzophenone. , 1,1,2,3,3,6-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',5',6',8',8'-hexamethyl-2-acetonaphthone, etc.; Aromatic and aliphatic carboxylic acids and their esters, such as benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenyl acetate, ethyl phenyl acetate, geranyl phenyl acetate, phenylethyl phenyl acetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, cinnamyl cinnamate, allyl phenoxy acetate, methyl salicylate, isoamyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate, etc.; Nitrogen-containing aromatic compounds, such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene, 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone, cinnamonitrile, 3-methyl-5-phenyl-2-pentenonitrile, 3-methyl-5-phenylpentanonitrile, methyl anthranilate, methyl-N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline, 6-isobutylquinoline, 6-sec-butylquinoline, 2-(3-phenylpropyl)pyridine, indole, skatole, 2-methoxy-3-isopropylpyrazine, 2-isobutyl-3-methoxypyrazine, etc.; Phenols, phenyl ethers and phenyl esters, such as estragole, anethole, eugenol, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, β-naphthyl methyl ether, β-naphthyl ethyl ether, β-naphthyl isobutyl ether, 1,4-dimethoxybenzene, eugenyl acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, p-cresyl phenyl acetate, etc.; 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, etc.; Lactones, for example 1,4-octanolide, 3-methyl-1,4-octanolide, 1,4-nonanolide, 1,4-decanolide, 8-decen-1,4-olide, 1,4-undecanolide, 1,4-dodecanolide, 1,5-decanolide, 1,5-dodecanolide, 4-methyl-1,4-decanolide, 1,15-pentadecanolide, cis- and trans-11-pentadecan-1,15- ... ns-12-pentadecen-1,15-olide, 1,16-hexadecanolide, 9-hexadecen-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, coumarin, 2,3-dihydrocoumarin, octahydrocoumarin, etc.

[0208] The aroma chemicals different from the compounds (I) and (II) in compositions A and B are preferably geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably with a cis content of more than 60% by weight), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butyl)-2- ... Phenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8- Tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, α-ionone, n-α-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene carboxaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadec-5-enone, (Z)-3-methylcyclopentadec-5-ene Non, 15-pentadec-11-enolide, 15-pentadec-12-enolide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-Dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably with a cis content of 70% by weight or more), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-( 4-tert-butylphenyl)-propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2-tert-butylcyclohexyl)acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-n-methylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0209] Non-fragrance Chemical Carriers A further embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and in the case of composition A additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one non-aroma chemical carrier.

[0210] The at least one non-aroma chemical carrier may be a compound, a mixture of compounds or other additive that exhibits no or no significant sensory properties. The non-aroma chemical carrier may serve to dilute and / or fix compound (I) (and in the case of composition A compound (II)) as defined above and optionally at least one further aroma chemical or any other ingredient if included in the composition.

[0211] A further embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) [and in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers] as defined above, and at least one non-aroma chemical carrier selected from the group consisting of solvents, surfactants and oil components.

[0212] According to a preferred embodiment of the present invention, the non-fragrance chemical carrier is selected from the following solvents, surfactants and oil components:

[0213] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one solvent.

[0214] In the context of the present invention, a "solvent" is one which serves to dilute the compound (I) (and in the case of composition A, compound (II)) used according to the invention and / or any further components of the composition which do not themselves have a fragrance.

[0215] The one or more solvents may be present in the composition in an amount of 0.01 to 99% by weight based on the composition. In a preferred embodiment of the present invention, the composition contains 0.1 to 90% by weight, preferably 0.5 to 80% by weight, of the solvent based on the total weight of the composition. The amount of the solvent can be selected depending on the composition. In one embodiment of the present invention, the composition contains 0.05 to 10% by weight, preferably 0.1 to 5% by weight, more preferably 0.2 to 3% by weight, based on the total weight of the composition. In one embodiment of the present invention, the composition contains 20 to 70% by weight, preferably 25 to 50% by weight, of the solvent based on the total weight of the composition.

[0216] Preferred solvents are ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), and benzyl benzoate (BB).

[0217] Particularly preferred solvents are selected from the group consisting of ethanol, propylene glycol, dipropylene glycol, triethyl citrate, benzyl benzoate, and isopropyl myristate.

[0218] In another preferred embodiment of the invention, the solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, triethyl citrate, and isopropyl myristate.

[0219] According to a further embodiment, the compound (I) or its stereoisomers or mixtures of its different stereoisomers or mixtures of different compounds (I) defined above (in the case of composition A, mixed with compound (II) or its stereoisomers or mixtures of its different stereoisomers) are used in surfactant-containing compositions according to the invention. Due to their characteristic fragrance properties and their substantivity, persistence and stability, the compound (I) or its stereoisomers or mixtures of its different stereoisomers or mixtures of different compounds (I) defined above (in the case of composition A, mixed with compound (II) or its stereoisomers or mixtures of its different stereoisomers) can be used, inter alia, to impart an odor, preferably a fragrance impression, to surfactant-containing compositions, such as cleaning agents (in particular laundry care products and multi-purpose cleaning agents). It can preferably be used to impart a long-lasting clean note to compositions containing surfactants.

[0220] Thus, one embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above and at least one surfactant.

[0221] The surfactants may be selected from anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants. Surfactant-containing compositions, such as shower gels, foam baths, shampoos, etc., preferably contain at least one anionic surfactant.

[0222] The compositions according to the invention usually contain surfactants in an amount of 0-40% by weight, preferably 0-20% by weight, more preferably 0.1-15% by weight, especially 0.1-10% by weight, in the aggregate, based on the total weight of the composition. Typical examples of non-ionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alkyl(enyl) oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkylglucamides, protein hydrolysates (especially wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. When the non-ionic surfactants contain polyglycol ether chains, these may have a conventional homolog distribution, but preferably have a narrow range homolog distribution.

[0223] The amphoteric surfactant has at least one quaternary ammonium group and at least one COO group in the molecule. (-) or SO3 (-) Group containing surface-active compounds. Particularly suitable zwitterionic surfactants are so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinates, such as cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, such as cocoacylaminopropyldimethylammonium glycinate, as well as 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines and cocoacylaminoethylhydroxyethylcarboxymethylglycinates, which contain 8 to 18 carbon atoms in the alkyl or acyl group. Particularly preferred are fatty acid amide derivatives known under the CTFA name of cocamidopropyl betaine.

[0224] Amphoteric surfactants are particularly suitable as cosurfactants. Amphoteric surfactants include those having C8 to C 18In addition to the alkyl or acyl group, it is a surface-active compound that contains at least one free amino group and at least one -COOH or SO3H group in the molecule and can form an intramolecular salt. Examples of suitable amphoteric surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl amino butyric acids, N-alkyl imino dipropionic acids, N-hydroxyethyl-N-alkyl amidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkyl amino propionic acids and alkyl amino acetic acids, with the alkyl group having about 8 to 18 carbon atoms. Particularly preferred amphoteric surfactants are N-cocoa alkyl amino propionates, cocoa acyl amino ethyl amino propionates and acyl sarcosines.

[0225] Anionic surfactants are characterized by a water-soluble anionic group, for example a carboxylate, sulfate, sulfonate or phosphate group, and a lipophilic group.Dermatologically safe anionic surfactants are known to many practitioners from relevant textbooks and are commercially available.These include, in particular, alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts, alkyl ether sulfates in the form of their alkali metal or ammonium salts, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, linear C 12 ~C 18 These are acyl taurate, sulfosuccinate and acyl glutamate which contain alkyl or acyl groups.

[0226] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more particularly chlorides and bromides such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride and trialkylmethylammonium chloride, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. In addition, easily biodegradable quaternary ester compounds can be used as cationic surfactants, such as dialkylammonium methosulfate and methylhydroxyalkyldialkyloxyalkylammonium methosulfate, which are commercially available under the name Stepantexe, and the corresponding products of the Dehyquart® series. "Esterquats" are generally understood to be quaternized fatty acid triethanolamine ester salts. They can impart a certain flexibility to the composition. They are known substances prepared by the relevant methods of organic chemistry. Other cationic surfactants suitable for use according to the invention are quaternized protein hydrolysates.

[0227] One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above, and at least one oil component.

[0228] The oil component is typically present in an amount of from 0.1 to 80% by weight, preferably from 0.5 to 70% by weight, more preferably from 1 to 60% by weight, even more preferably from 1 to 50% by weight, particularly from 1 to 40% by weight, more particularly from 5 to 25% by weight, and particularly from 5 to 15% by weight, based on the total weight of the composition.

[0229] The oil component may be, for example, Guerbet alcohols based on aliphatic alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, and other further esters, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearate ... The oleyl ester may be selected from tearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, and erucyl erucate. 18 ~C 38 Alkyl-hydroxycarboxylic acids and linear or branched C6-C 22 Esters with fatty alcohols, more specifically dioctyl malate, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g. propylene glycol, dimer dials or trimer triols), C6-C 10 Triglycerides based on fatty acids, C6-C 18 Liquid mono-, di- and triglyceride mixtures based on fatty acids, C6-C 22Esters of fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups with dicarboxylic acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C 22 Fatty alcohol carbonates, for example Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, such as dicaprylyl carbonate (Cetiol® CC), benzoic acid and linear and / or branched C6-C 22 Also suitable are esters with alcohols (e.g. Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, such as dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof.

[0230] Antioxidants One embodiment of the present invention relates to a composition comprising compound (I) or a stereoisomer thereof or a mixture of its different stereoisomers or a mixture of different compounds (I) (and, in the case of composition A, additionally compound (II) or a stereoisomer thereof or a mixture of its different stereoisomers) as defined above, and at least one antioxidant.

[0231] Antioxidants are capable of inhibiting or preventing undesirable changes caused by the action of oxygen and other oxidative processes in the composition to be protected. The effect of antioxidants is in most cases to act as free radical scavengers of the free radicals generated during autoxidation.

[0232] The antioxidant is, for example, selected from the group consisting of: Amino acids (e.g., glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan, etc.) and their derivatives, Imidazoles (e.g. urocanic acid) and their derivatives, Peptides such as D,L-carnosine, D-carnosine, L-carnosine (=β-alanyl-L-histidine) and their derivatives, Carotenoids, carotenes (e.g. α-carotene, β-carotene, lycopene, lutein) or derivatives thereof, Chlorogenic acid and its derivatives, Lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters) and their salts, Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts), Sulfoximine compounds (e.g. buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa-, and heptathionine sulfoximine), (Metal) chelating agents (e.g. alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), Humic acid, bile acids, bile extract, bilirubin, biliverdin, boldine (= alkaloids derived from the plant Peumus boldus), boldo extract, EDTA, EGTA and their derivatives, Unsaturated fatty acids and their derivatives (e.g., gamma-linolenic acid, linoleic acid, oleic acid), Folic acid and its derivatives, Ubiquinone and ubiquinol and their derivatives, Vitamin C and derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), Tocopherol and derivatives (e.g. vitamin E acetate), Vitamin A and derivatives (e.g. vitamin A palmitate), Benzoin gum coniferyl benzoate, rutin acid and its derivatives, α-glycosyl rutin, ferulic acid, furfurylidene glucitol, Butylated hydroxytoluene (BHT), Butylated hydroxyanisole (BHA), Nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, Superoxide dismutase, Zinc and its derivatives (e.g. ZnO, ZnSO4), Selenium and its derivatives (e.g. selenomethionine) Stilbene and its derivatives (e.g. stilbene oxide, trans-stilbene oxide).

[0233] In a preferred embodiment, the antioxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ascorbyl palmitate, and tocopherol.

[0234] The composition according to the present invention may contain the antioxidant in an amount of 0.001 to 25% by weight, preferably 0.005 to 10% by weight, preferably 0.01 to 8% by weight, more preferably 0.025 to 7% by weight, preferably 0.05 to 5% by weight, based on the total weight of the composition.

[0235] Deodorizing agent One embodiment of the present invention relates to a composition comprising a compound (I) as defined, or a stereoisomer thereof, or a mixture of its different stereoisomers, or a mixture of different compounds (I) (and, in the case of composition A, also a compound (II) or a stereoisomer thereof, or a mixture of their different stereoisomers), and at least one deodorant active.

[0236] Compound (I) or its stereoisomers or a mixture of its different stereoisomers or a mixture of different compounds (I) (in the case of composition A, with compound (II) or its stereoisomers or a mixture of their different stereoisomers) as defined above can be used to impart a clean and long-lasting note to deodorant compositions as well as to the skin treated with such compositions.

[0237] Deodorant compositions (deodorants and antiperspirants) neutralize, mask or eliminate body odor, which is caused by the action of skin bacteria on apocrine sweat, resulting in the formation of unpleasant-smelling decomposition products.

[0238] In a preferred embodiment of the present invention, the at least one deodorant active is selected from the group consisting of antiperspirants, esterase inhibitors and antimicrobial agents.

[0239] Suitable antiperspirants can be selected from the group consisting of aluminum, zirconium or zinc salts, such as aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complex compounds, for example with 1,2-propylene glycol, aluminum hydroxyalanthoate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, tetrachloro(Al / zirconium) hydrate, aluminum zirconium pentachlorohydrate and their complex compounds, for example with amino acids, such as glycine. Aluminum chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and their complex compounds are preferably used.

[0240] In a preferred embodiment of the invention, the composition comprises at least one antiperspirant selected from the group consisting of aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxyalanthoate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium pentachlorohydrate and aluminum zirconium pentachlorohydrate.

[0241] The composition according to the present invention may contain the antiperspirant in an amount of 1 to 50% by weight, preferably 5 to 30% by weight, more specifically 10 to 25% by weight, based on the solid content of the composition.

[0242] When sweat is present in the armpit area, bacteria form extracellular enzymes, esterases, mainly proteases and / or lipases, which break down the esters present in sweat, releasing odor in the process.Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate.Esterase inhibitors inhibit enzyme activity, thereby reducing odor generation.The cleavage of citrate esters probably releases free acid, lowering the pH value of the skin to such an extent that enzymes are inactivated by acylation. Other esterase inhibitors are, for example, sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and their esters, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester and zinc glycine.

[0243] In a preferred embodiment of the invention, the composition comprises at least one esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester, zinc glycine.

[0244] The composition according to the present invention may contain the esterase inhibitor in an amount of 0.01 to 20, preferably 0.1 to 10, more specifically 0.5 to 5% by weight based on the solids content of the composition.

[0245] The term "antimicrobial agent" as used herein includes substances that have bactericidal and / or bacteriostatic properties. Typically, these substances include, for example, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenyl)-4-phenylpropanediol, 4-chlorophenyl-5 ... (noxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides, such as salicylic acid-n-octylamide or salicylic acid-n-decylamide, act on gram-positive bacteria.

[0246] In a preferred embodiment, the antimicrobial agent is chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1- methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamide.

[0247] The composition according to the present invention may contain the antibacterial agent in an amount of 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the solid content of the composition.

[0248] The compositions according to the invention may contain, for example: antiseptics, abrasives, anti-acne agents, agents for combating skin ageing, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, inflammation suppressants, irritation relieving agents, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, care agents, depilatories, emulsifiers, enzymes, essential oils, fibres, film-forming agents, fixing agents, foaming agents, foam stabilising agents, foam inhibitors, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, agents for smoothing hair, hair styling agents, moisture donors, moisturising substances, humectants, bleaching agents, strengthening agents, stain removers, optical brighteners, impregnating agents, antifouling agents, friction reducers, lubricants, moisturising creams, ointments, opacifiers. The composition may further comprise one or more substances such as a plasticizer, a coating agent, a polishing agent, a gloss agent, a polymer, a powder, a protein, a refatting agent, an exfoliant, a silicone, a skin soothing agent, a skin cleansing agent, a skin care agent, a skin healing agent, a skin whitening agent, a skin protecting agent, a skin softener, a cooling agent, a skin cooling agent, a warming agent, a skin warming agent, a stabilizer, an ultraviolet absorbing agent, an ultraviolet screening agent, a softener, a suspending agent, a skin tanning agent, a thickener, a vitamin, a wax, a fat, a phospholipid, a saturated fatty acid, a mono- or polyunsaturated fatty acid, an alpha-hydroxy acid, a polyhydroxy fatty acid, a liquefying agent, a dye, a color protecting agent, a pigment, an anticorrosive agent, a polyol, an electrolyte, or a silicone derivative.

[0249] The compound (I) or its stereoisomers or mixtures of its different stereoisomers or mixtures of different compounds (I) (in the case of composition A, with compound (II) or its stereoisomers or mixtures of its different stereoisomers) described herein can be used in a wide range of compositions, preferably perfuming compositions, more preferably fragrance compositions. It is emphasized that the olfactory properties of compound (I) (and compound (II) in the case of composition A) and the properties of this substance (solubility in conventional solvents and compatibility with further constituents conventionally used in such compositions) make them particularly suitable for the mentioned purposes of use and combinations for use in compositions.

[0250] Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions), oral and dental hygiene products, hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, food products, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0251] The perfume compositions may be selected from fine fragrances, air fresheners in liquid form, in gel form or applied to a solid carrier, aerosol sprays, scented cleaning products, perfumed candles and oils such as lamp oils or massage oils.

[0252] Examples of fine fragrances are perfume extracts, Eau de Parfum, Eau de Toilette, Eau de Cologne, Eau de Solide and Extrait Parfum.

[0253] Body care compositions include cosmetic compositions, including aftershave lotions, preshave products, splash colognes, bar and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil, and water-in-oil-in-water cosmetic emulsions, such as skin creams and lotions, facial creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, and cosmetic compositions, such as ... hair care products such as hair sprays, hair gels, hair setting lotions, hair conditioners, hair shampoos, permanent and semi-permanent hair dyes, hair styling compositions such as cold wave perms and hair smoothing compositions, hair tonics, hair creams and hair lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, decorative cosmetic products such as eyeliners, eye shadows, nail polishes, make-up products, lipsticks and mascaras, etc.

[0254] Oral and dental hygiene products may be selected from toothpaste, dental floss, mouthwash, breath fresheners, dental foams, dental gels and dental strips.

[0255] The hygiene products may be selected from incense sticks, insecticides, repellents, propellants, rust removers, scented freshening wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, pocket tissues, dishwashing agents and deodorants.

[0256] Cleaning compositions such as cleaners for solid surfaces may be selected from scented acidic, alkaline and neutral cleaners, e.g. floor cleaners, window cleaners, dishwashing compositions both for hand and machine washing, bathroom and sanitary cleaners, scouring milks, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polishes, floor waxes, shoe creams, disinfectants, surface disinfectants and sanitary cleaners, brake cleaners, pipe cleaners, limescale removers, grill and oven cleaners, algae and moss removers, mould removers, facade cleaners.

[0257] Fabric detergent compositions may be selected from liquid detergents, powder detergents, laundry pre-treatments such as bleaches, soaking agents and stain removers, fabric softeners, laundry soaps, laundry tablets.

[0258] Food means any raw, cooked or processed edible substance, ice, beverage or ingredient, or chewing gum, gummy candies, jellies and confectioneries, which are used or intended to be used in whole or in part for human consumption.

[0259] A dietary supplement is a product intended for ingestion that contains dietary ingredients intended to add additional nutritional value to the diet. The dietary ingredients can be one or any combination of the following substances: vitamins, minerals, herbs or other botanicals, amino acids, dietary substances, concentrates, metabolites, ingredients or extracts used by humans to supplement the diet by increasing total dietary intake. Dietary supplements come in many forms, including tablets, capsules, softgels, gel capsules, liquids or powders.

[0260] Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment or prevention of disease, as well as articles (other than food) intended to affect the structure or any function of the human or other animal body.

[0261] Crop protection compositions include compositions intended for the management of plant diseases, weeds and other pests (both vertebrate and invertebrate) that damage agricultural crops and forests.

[0262] The compositions according to the invention may contain, for example: antiseptics, abrasives, anti-acne agents, agents for combating skin ageing, antibacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, inflammation suppressing agents, irritation soothing agents, antimicrobial agents, antioxidants, astringents, sweat-inhibiting agents, preservatives, antistatic agents, binding agents, buffering agents, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilatories, surfactants, deodorants, antiperspirants, emulsifiers, enzymes, essential oils, fibres, film-forming agents, fixing agents, foaming agents, foam stabilising agents, foam suppressing agents, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair styling agents, agents for smoothing hair, moisture donating agents, moisturising substances, humectants, bleaching agents, strengthening agents, stain removers, optical brighteners, impregnating agents, The composition may further comprise one or more substances such as a stain repellent, a friction reducer, a lubricant, a moisturizing cream, an ointment, an opacifier, a plasticizer, a coating, a polishing agent, a glossing agent, a polymer, a powder, a protein, a refatting agent, an exfoliant, a silicone, a skin soothing agent, a skin cleansing agent, a skin care agent, a skin healing agent, a skin whitening agent, a skin protecting agent, a skin softener, a cooling agent, a skin cooling agent, a warming agent, a skin warming agent, a stabilizer, an ultraviolet absorbing agent, an ultraviolet screening agent, a softener, a suspending agent, a skin tanning agent, a thickener, a vitamin, a wax, a fat, a phospholipid, a saturated fatty acid, a mono- or polyunsaturated fatty acid, an alpha-hydroxy acid, a polyhydroxy fatty acid, a liquefying agent, a dye, a color protecting agent, a pigment, an anticorrosive agent, a polyol, an electrolyte, or a silicone derivative.

[0263] Compound (I) or a mixture of its stereoisomers or its different stereoisomers or a mixture of different compounds (I) described herein (and in the case of composition A, compound (II) or a mixture of its stereoisomers or its different stereoisomers) can be incorporated into the composition by simply mixing directly with the base composition lacking only this / these compounds. Alternatively, compound (I) or a mixture of its stereoisomers or its different stereoisomers or a mixture of different compounds (I) described herein (and in the case of composition A, compound (II) or a mixture of its stereoisomers or its different stereoisomers) can be mixed simultaneously or sequentially with the other components of the composition or with a preformed mixture of some of the other components.

[0264] The compound (I) or its stereoisomer or a mixture of its different stereoisomers or a mixture of different compounds (I) (in the case of composition A, a mixture with compound (II) or its stereoisomer or a mixture of its different stereoisomers) as defined above can be at an early stage encapsulated in an encapsulating material, such as polymers, capsules, microcapsules and nanocapsules, liposomes, film-forming agents, adsorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or can be chemically bound to a substrate adapted to release compound (I) upon application of an external stimuli such as light, enzymes, etc., which then mix with the composition.

[0265] The compound (I) or its stereoisomers or mixtures of its different stereoisomers or mixtures of different compounds (I) described herein (and in the case of composition A, compound (II) or its stereoisomers or mixtures of its different stereoisomers) and compositions comprising these compounds according to the invention may also be in microencapsulated, spray-dried, in the form of inclusion complexes or in the form of extruded products. Their properties can be further optimized by so-called "coating" with materials suitable for a better targeting of the release of the scent; for this purpose, preferably waxy synthetic substances are used, such as, for example, polyvinyl alcohol.

[0266] Microencapsulation can be carried out, for example, by the so-called coacervation method, using capsule materials, for example made of polyurethane-like substances or soft gelatin. Spray-dried perfume oils can be produced, for example, by spray-drying emulsions or dispersions comprising compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as described herein (and in the case of composition A, compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof) or compositions of the invention as described herein, where carrier materials that can be used include modified starches, proteins, dextrins and vegetable gums. Inclusion complexes can be prepared, for example, by introducing a dispersion of the fragrance composition and a cyclodextrin or urea derivative into a suitable solvent, for example water. The extrusion product can be produced by melting compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) (in the case of composition A, a mixture with compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof) described herein or a composition of the invention described herein with a suitable waxy substance and, optionally, in a suitable solvent, for example isopropanol, by extrusion and subsequent solidification.

[0267] Generally, the total amount of one or more compounds (I) (and in the case of composition A, compound (II)) in the composition according to the invention is typically adapted to the specific intended use or intended application and can therefore vary within a wide range. As a rule, standard commercial amounts customarily used for fragrances are used.

[0268] The composition according to the present invention may contain the compound of formula (I) (and (II) in the case of composition A) in a total amount of 0.001 to 99.9 wt.%, preferably 0.01 to 90 wt.%, more preferably 0.05 to 80 wt.%, particularly 0.1 to 60 wt.%, more particularly 0.1 to 40 wt.%, for example 0.1 to 10 wt.% or 0.1 to 15 wt.%, based on the total weight of the composition.

[0269] In one embodiment of the invention, the composition comprises the compound of formula (I) (and (II) in the case of composition A) in a total amount of 0.001 to 5% by weight, preferably 0.01 to 2% by weight, based on the total weight of the composition.

[0270] Some of the compounds (I) are novel. Thus, the present invention also relates to compounds of formula (I) [ka] [In the formula, R 1 is C1-C3 alkyl, formyl, or ethylcarbonyl; or to a stereoisomer thereof or to a mixture of different stereoisomers thereof or to a mixture of different compounds (I).

[0271] Preferably, R 1 is C1-C3 alkyl or ethylcarbonyl, more preferably methyl, ethyl, or ethylcarbonyl; specifically, ethyl.

[0272] As already described for compositions A and B, in the compound of formula (I), -OR 1 The group is preferably attached at the exo position.

[0273] The compounds of formula (I) and mixtures of compounds (I) and (II) not only have a pleasant odor, especially a fragrance; they are also readily available. In particular, they can be easily produced with reduced CO2 emissions, for example by using renewable resources and / or utilizing industrial by-products.

[0274] The present invention is further illustrated by the following examples. EXAMPLES

[0275] 1. Preparation Example 1.1 Carbeno[compound of formula (II)] and 2-hydroxy-1,4-cineole[compound of formula (I)] [wherein R 1is H) A mixture containing 87% by weight of carbenox and 12% by weight of 2-hydroxy-1,4-cineole was obtained as a by-product in the synthesis of cinmethylin starting from terpinen-4-ol via its epoxidation and acidic rearrangement of the epoxide.

[0276] 1.2 Preparation of a mixture of carbenones and (4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-yl) acetate (acetate of 2-hydroxy-1,4-cineole) 20 g (1.00 eq.) of the mixture of Example 1.1 and 0.08 eq. of N,N-dimethylpyridin-4-amine (DMAP) were placed in a 100 mL round-bottom flask and heated to 60° C. To this mixture, 1.25 eq. of acetic anhydride were added within 5 min and the mixture was stirred at 60° C. for 5 h. Another 0.5 eq. of acetic anhydride was added and the mixture was stirred at 60° C. for 20 h. After cooling to room temperature, the reaction mixture was diluted with 25 mL of ethyl acetate and quenched with saturated aqueous NaHCO3 solution. The phases were separated, the organic phase was washed with saturated aqueous NaHCO3 solution and NaCl solution, dried over Na2SO4 and the solvent was removed under reduced pressure. Two batches of the crude product of this reaction were purified by distillation to give fractions with weight ratios of carbenone to (4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-yl)acetate ranging from 94:5 to 84:15 as colorless liquids with purities of at least 99.0 GC-a% (GC-a% = percent of GC area).

[0277] 1.3 Preparation of a mixture of carbenones and 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (=ethyl ether of 2-hydroxy-1,4-cineole) Carbenone and 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (=ethyl ether of 2-hydroxy-1,4-cineole; obtained according to Example 1.5) were mixed in the desired ratio.

[0278] 1.4 Preparation of (4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-yl) acetate (acetate of 2-hydroxy-1,4-cineole) 50 g (1.00 equiv.) of 2-hydroxy-1,4-cineole and 0.08 equiv. of N,N-dimethylpyridin-4-amine (DMAP) were added to 200 mL of tetrahydrofuran in a 1000 mL round-bottom flask and heated to 60° C. To this mixture, 1.25 equiv. of acetic anhydride were added within 5 min and the mixture was stirred at 60° C. for 5 h. After cooling to room temperature, the reaction mixture was diluted with 200 mL of ethyl acetate and quenched with 100 mL of saturated aqueous NaHCO3. The phases were separated, the organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by distillation to give the title compound as a colorless liquid with a purity of >99.9 GC-a%. 1 H NMR(500MHz,CDCl3)δ4.88(dd,J=7.3,2.6Hz,1H),2.18(dd,J=13.2,7.3Hz,1H),2 .13-2.08(m,1H),2.07(s,3H),1.65-1.43(m,5H),1.39(s,3H),1.02-0.92(m,6H). 13 C NMR(126MHz,CDCl3)δ170.8,88.8,84.4,78.4,77.4,77.2,76.9,43.3,33.4,32.5,31.2,21.2,18.2,17.9,16.4. MS(PCI,C 12 H 20 O3) Calculated value: 213.2 [M+H] + , Measured value 213.2 [M+H] +

[0279] 1.5 Preparation of 2-ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (=ethyl ether of 2-hydroxy-1,4-cineole) In a 500 mL round bottom flask, 1.5 equivalents of sodium hydride (60% dispersion in mineral oil) was added to 50 mL of tetrahydrofuran. 20 g (1.00 equivalents) of 2-hydroxy-1,4-cineole in 30 mL of tetrahydrofuran was added to this mixture within 15 minutes. The resulting reaction mixture was stirred at room temperature for another 30 minutes. 1.5 equivalents of iodoethane were added within 20 minutes. The mixture was heated to 40° C. and stirred for 23 hours. The mixture was cooled to room temperature and quenched by adding 50 mL of water. The mixture was extracted twice with 60 mL of 2-methoxy-2-methylpropane. The combined organic layers were washed with saturated aqueous NaHCO3 and NaCl solutions, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation and column chromatography on SiO2 (cyclohexane / ethyl acetate 95:5 to 90:10) to afford the title compound as a colorless liquid with a purity of >99.9 GC-a%. 1 H NMR(500MHz,CDCl3)δ3.53-3.43(m,2H),3.35(dq,J=9.3,7.0Hz,1H),2.09(h,J=6.9Hz,1H),1.96(dd,J=12.5,6.8 Hz,1H),1.55(ddd,J=8.7,6.6,3.0Hz,2H),1.50-1.40(m,6H),1.18(t,J=7.0Hz,3H),0.97(dd,J=6.9,2.5Hz,6H). 13 C NMR(126MHz,CDCl3)d88.5,85.4,83.6,64.1,42.7,33.9,32.7,31.7,26.9,18.3,18.0,16.5,15.4. MS(PCI,C 12 H 22 O2) Calculated value 199.2 [M+H] + , Measured value 199.2 [M+H] +

[0280] 2. Olfactory Test To test the odor quality and intensity of the mixture of compounds (I) and (II) or compound (I) alone, a scent strip test was performed.

[0281] For this purpose, strips of absorbent paper were immersed in a mixture of the compounds (I) and (II) to be tested or in a solution of compound (I) at 1-10% by weight in triethyl citrate. After evaporation of the solvent (approximately 30 seconds), the odor impression was evaluated by olfaction by a trained perfumer.

[0282] The results of the odor testing are summarized in Table 1.

[0283] [Table 1]

[0284] [Table 2]

[0285] [Table 3]

[0286] Commercial products and advantageous fragrance compositions "Solution A" is the neat product of Example 1.1. "Solution B" is the neat product of Example 1.2. "Solution C" is the neat product of Example 1.3. "Solution D" is the neat product of Example 1.4. "Solution E" is the neat product of Example 1.5. "Solution F" is the neat product of Example 1.6. "Solution G" is the neat product of Example 1.7. "Solution H" is the neat product of Example 1.8.

[0287] Advantageous fragrance compositions: Solution A described above was formulated into a composition according to Table 2. The amounts shown in Table 2 are in grams.

[0288] [Table 4]

[0289] Solution A described above was formulated into a composition according to Table 3. The amounts shown in Table 3 are in grams.

[0290] [Table 5]

[0291] Fragrance composition 3 corresponds to fragrance composition 1A in which solution A is replaced with an equal amount of solution B. Fragrance composition 4 corresponds to fragrance composition 1B in which solution A is replaced with an equal amount of solution B. Fragrance composition 5 corresponds to fragrance composition 2A in which solution A is replaced with an equal amount of solution B. Fragrance composition 6 corresponds to fragrance composition 2B in which solution A is replaced with an equal amount of solution B.

[0292] Fragrance composition 7 corresponds to fragrance composition 1A in which solution A has been replaced with an equal amount of solution C. Fragrance composition 8 corresponds to fragrance composition 1B in which solution A has been replaced with an equal amount of solution C. Fragrance composition 9 corresponds to fragrance composition 2A in which solution A has been replaced with an equal amount of solution C. Fragrance composition 10 corresponds to fragrance composition 2B in which solution A has been replaced with an equal amount of solution C.

[0293] Fragrance composition 11 corresponds to fragrance composition 1A in which solution A has been replaced with an equal amount of solution D. Fragrance composition 12 corresponds to fragrance composition 1B in which solution A has been replaced with an equal amount of solution D. Fragrance composition 13 corresponds to fragrance composition 2A in which solution A has been replaced with an equal amount of solution D. Fragrance composition 14 corresponds to fragrance composition 2B in which solution A has been replaced with an equal amount of solution D.

[0294] Fragrance composition 15 corresponds to fragrance composition 1A where solution A is replaced with an equal amount of solution E. Fragrance composition 16 corresponds to fragrance composition 1B where solution A is replaced with an equal amount of solution E. Fragrance composition 17 corresponds to fragrance composition 2A where solution A is replaced with an equal amount of solution E. Fragrance composition 18 corresponds to fragrance composition 2B where solution A is replaced with an equal amount of solution E.

[0295] Fragrance composition 19 corresponds to fragrance composition 1A in which solution A has been replaced with an equal amount of solution F. Fragrance composition 20 corresponds to fragrance composition 1B in which solution A has been replaced with an equal amount of solution F. Fragrance composition 21 corresponds to fragrance composition 2A in which solution A has been replaced with an equal amount of solution F. Fragrance composition 22 corresponds to fragrance composition 2B in which solution A has been replaced with an equal amount of solution F.

[0296] Fragrance composition 23 corresponds to fragrance composition 1A in which solution A has been replaced with an equal amount of solution G. Fragrance composition 24 corresponds to fragrance composition 1B in which solution A has been replaced with an equal amount of solution G. Fragrance composition 25 corresponds to fragrance composition 2A in which solution A has been replaced with an equal amount of solution G. Fragrance composition 26 corresponds to fragrance composition 2B in which solution A has been replaced with an equal amount of solution G.

[0297] Fragrance composition 27 corresponds to fragrance composition 1A in which solution A has been replaced with an equal amount of solution H. Fragrance composition 28 corresponds to fragrance composition 1B in which solution A has been replaced with an equal amount of solution H. Fragrance composition 29 corresponds to fragrance composition 2A in which solution A has been replaced with an equal amount of solution H. Fragrance composition 30 corresponds to fragrance composition 2B in which solution A has been replaced with an equal amount of solution H.

[0298] The compositions according to Tables 2 and 3, i.e. 1A, 1B, 2A and 2B and fragrance compositions 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 29 and 30 are suitable for use in pump deodorant sprays, clean hair conditioners, facial gels, foam bath concentrates, self-foaming body washes, spray sun care emulsions, spray sun protection emulsions, facial emollient gels, two-phase oil foam baths, shampoos, shower baths, aqueous / alcoholic AP / deodorant pump sprays, aerosols, aqueous / alcoholic AP / deodorant roll-ons, "Out of bed" deodorants, and the like. The composition may be included in various compositions selected from the group consisting of: hair conditioning gel, shaving foam, baby shampoo for sensitive skin, body wash for sensitive skin, shine enhancing shampoo for sensitive scalp, deodorant stick, baby wipes, after shave balsam, face gel, face day cream, face wash, body lotion, SPF50+ sunscreen, spray lotion, hand dishwashing detergent (non-concentrated), hand dishwashing detergent (concentrated), sanitary equipment cleaner (concentrated), all-purpose cleaner, antibacterial fabric softener, detergent composition, powder detergent composition and liquid detergent composition.

[0299] Those skilled in the art will be familiar with the various general formulations of the above mentioned products.

[0300] Compositions 1A, 1B, 2A, 2B, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 29, and 30 may be formulated in specific formulations, for example, as disclosed in Tables 1 to D13, pages 6 to 46 of IP.com Number: IPCOM000258614D entitled New Aroma Chemicals, where "Fragrance Composition 1A" is replaced with an equal amount of Composition 1A, 1B, 2A, 2B, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 29, or 30.

Claims

1. (a) Formula (I) 【Chemistry 1】 [In the formula, R １ is hydrogen, C １ ~C ４ Alkyl, formyl, or C １ ~C ３ alkylcarbonyl; or with a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I); (b) Formula (II) 【Chemistry 2】 or a stereoisomer thereof or a mixture of different stereoisomers thereof 10. Use of a composition comprising:

2. In the compound of formula (I), R １ The use according to claim 1 , wherein is hydrogen.

3. In the compound of formula (I), R １ is formyl or C １ ~C ３ Alkylcarbonyl, preferably C １ ~C ３ 2. The use according to claim 1, wherein the alkylcarbonyl is more preferably methylcarbonyl or ethylcarbonyl, in particular methylcarbonyl.

4. In the compound of formula (I), R １ But C １ ~C ４ Alkyl, preferably C １ ~C ３ 2. The use according to claim 1, wherein the alkyl is in particular methyl or ethyl, particularly ethyl.

5. In the compound of formula (I), -OR １ 2. The use according to claim 1, wherein the group is attached in the exo position.

6. 2. The use according to claim 1, wherein said compound of formula (I) and said compound of formula (II) are used in a molar ratio of from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 1:1 to 1:50, in particular from 1:2 to 1:30, more particularly from 1:2 to 1:

15.

7. Use according to any one of claims 1 to 6 as a fragrance.

8. Use of a composition according to any one of claims 1 to 6 for modifying and / or enhancing the aroma of a composition; in particular for modifying and / or enhancing the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition.

9. (a) a compound of formula (I) according to claim 1 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I), (b) a compound of formula (II) according to claim 1 or a stereoisomer thereof or a mixture of different stereoisomers thereof; A composition comprising:

10. In the compound of formula (I), R １ is hydrogen, said compound of formula (I) and said compound of formula (II) are present in a molar ratio of from 3:1 to 1:100, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:50, in particular from 1:2 to 1:30, more particularly from 1:2 to 1:

15.

11. In the compound of formula (I), R １ 10. A composition according to claim 9, wherein when is not hydrogen, said compound of formula (I) and said compound of formula (II) are present in a molar ratio of from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 1:1 to 1:50, in particular from 1:2 to 1:30, more particularly from 1:2 to 1:

15.

12. 10. The composition of claim 9, further comprising at least one additional ingredient selected from the group consisting of fragrance chemicals different from compounds (I) and (II), non-fragrance chemical carriers, antioxidants, and deodorizing actives; in particular from the group consisting of fragrance chemicals different from compounds (I) and (II), surfactants, oil components, solvents, antioxidants, and deodorizing actives.

13. 10. A composition comprising a compound of formula (I) according to claim 1 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I); and at least one further component selected from the group consisting of fragrance chemicals different from compound (I), non-fragrance chemical carriers, antioxidants and deodorant actives; in particular from the group consisting of fragrance chemicals different from compound (I), surfactants, oil components, solvents, antioxidants and deodorant actives, When the composition contains menthol, 4-hydroxycarbomenthone, 3,7-dimethyl-2,6-octadiene, krypton, p-menthane-1,2-diol, toluene, dichloromethane, tetrahydrofuran, dimethylformamide, hexane, or chloroform, R １ is not hydrogen; When the composition contains dichloromethane or hexane, R １ is acetyl (methylcarbonyl; —C(O)CH ３ ) provided that it is not; R １ is hydrogen and said aroma chemical different from compound (I) is a compound of formula (II) as defined in claim 1, wherein said compound of formula (I) and said compound of formula (II) are present in a molar ratio of from 3:1 to 1:>1, preferably from 3:1 to 1:100, more preferably from 1:1 to 1:100, even more preferably from 1:1 to 1:50, in particular from 1:2 to 1:30, more particularly from 1:2 to 1:

15.

14. In the compound of formula (I), R １ But C １ ~C ４ Alkyl, formyl, or C １ ~C ３ alkylcarbonyl; preferably R １ is acetyl or C １ ~C ３ alkyl, more preferably C １ ~C ３ The composition of claim 13 wherein the alkyl is alkyl.

15. 13. The composition of claim 12, wherein the non-fragrance chemical carrier comprises one or more solvents selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

16. The aroma chemical substance different from compounds (I) and (II) is selected from the group consisting of geranyl acetate, α-hexyl cinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis content of more than 60% by weight), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, and the like. ethanol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4- tert-Butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, α-ionone, n-α-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadec-5-enone, (Z)-3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide, 15-pentadec- 12-enolide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably containing 70% by weight or more of cis-isomer), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)propanal, ethylenedioxymethyl ...

13. The composition of claim 12, wherein the acetylated methyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl)acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-n-methylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

17. 17. The composition according to any one of claims 9 to 16, selected from the group consisting of perfume compositions, body care compositions, oral or dental hygiene products, hygiene products, cleaning compositions, fabric detergent compositions, fragrance dispenser compositions, food products, dietary supplements, pharmaceutical compositions, and crop protection compositions.

18. Use of the compound of formula (I) according to claim 1 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) as aroma chemicals, in particular as fragrances; １ Uses that do not include use of compounds of formula (I) wherein is hydrogen.

19. 1. Use of a compound of formula (I) according to claim 1 or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I) for modifying and / or improving the aroma of a composition; in particular for modifying and / or improving the fragrance impression of a composition; in particular for modifying the odor characteristics of a ready-to-use fragrance composition, The use is for modifying and / or enhancing the aroma of menthol or for modifying and / or enhancing the aroma of an essential oil obtained from the rhizomes of Ferula Jaeschkeana. １ does not include the use of a compound of formula (I) wherein is hydrogen.

20. In the compound of formula (I), R １ But C １ ~C ４ Alkyl, formyl, or C １ ~C ３ alkylcarbonyl; preferably R １ But C １ ~C ４ Alkyl, or C １ ~C ３ alkylcarbonyl, more preferably C １ ~C ３ 20. The use according to claim 18 or 19, wherein the alkyl is alkyl.

21. In the compound of formula (I), R １ is hydrogen, the use being for modifying and / or enhancing the aroma of menthol or as an aroma chemical of an essential oil obtained from the rhizomes of Ferula Jaeschkeana or for modifying and / or enhancing the aroma of an essential oil obtained from the rhizomes of Ferula Jaeschkeana; １ 20. The use according to claim 18 or 19, which does not encompass the use of compounds of formula (I) in which is hydrogen.

22. Formula (I) 【Transformation 3】 [In the formula, R １ is C １ ~C ３ alkyl, formyl, or ethylcarbonyl; or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different compounds (I).

Images