Oct-5-en-2-yl acetate and mixtures thereof as aroma ingredient

Abstract

The present invention relates to oct-5-en-2-yl acetate, to the use thereof as an aroma chemical, to the use thereof to impart an aroma to a composition, and to a method for imparting an aroma to a composition. The present invention further relates to a mixture comprising oct-5-en-2-yl acetate and 2-octyl acetate, to the use of said mixture as an aroma chemical, to the use of said mixture to impart an aroma to a composition, and to a method for imparting an aroma to a composition. The present invention is also directed to the use of oct-5-en-2-yl acetate for boosting or modifying the aroma of 2-octyl acetate. The present invention is further directed to a composition comprising oct-5-en-2-yl acetate or the mixture of oct-5-en-2-yl acetate and 2-octyl acetate.

Description

[0001] 230961W001

[0002] Oct-5-en-2-yl acetate and mixtures thereof as aroma ingredient

[0003] FIELD OF INVENTION

[0004] The present invention relates to oct-5-en-2-yl acetate of formula (I) as shown below, to the use thereof as an aroma chemical, to the use thereof to impart an aroma to a composition, in particular a floral violet note, fruity note, marine note, technical metallic note or any combination of two or more of these impressions, and to a method for imparting an aroma to a composition by incorporating oct-5-en-2-yl acetate into a composition to be aromatized or by mixing oct-5-en-2-yl acetate simultaneously or sequentially with a part or with all other components of the desired composition. The present invention further relates to a mixture comprising oct-5-en-2-yl acetate of formula (I) and 2-octyl acetate of formula (II) as shown below, to the use of said mixture as an aroma chemical, to the use of said mixture to impart an aroma to a composition, and to a method for imparting an aroma to a composition by incorporating said mixture into a composition to be aromatized or by mixing said mixture simultaneously or sequentially with a part or with all other components of the desired composition. The present invention is also directed to the use of oct-5-en-2-yl acetate for boosting or modifying the aroma of 2-octyl acetate. The present invention is further directed to a composition comprising oct-5-en-2-yl acetate of formula (I) or the mixture of oct-5-en-2- yl acetate and 2-octyl acetate.

[0005] BACKGROUND

[0006] Aroma chemicals, especially fragrances, are of great interest, especially in the field of cosmetics, cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, often limited in their available amount and, on account of fluctuations in environmental conditions, are also subject to variations in their content, purity etc. To circumvent these undesirable factors, it is therefore of great interest to create synthetic substances which have organoleptic properties that resemble more expensive natural fragrances, or which have novel and interesting sensory profiles.

[0007] Despite a large number of already existing synthetic aroma chemicals, there is a constant need for new components in order to be able to satisfy the multitude of properties desired for extremely diverse areas of application. These include, firstly, the sensory properties, i.e. the compounds should have advantageous odiferous (olfactory) properties. Furthermore, aroma chemicals should also have additional positive secondary properties, such as e.g. an efficient preparation method, the possibility of providing better sensory profiles as a result of synergistic effects with other aroma chemicals, a higher stability under certain application conditions, a higher extendibility, a higher substantivity.

[0008] M / BASFTR-2475-PC 230961W001

[0009] 2

[0010] Such properties are of special interest for compositions such as for example body care compositions, hygiene articles, cleaning compositions, textile detergent compositions and compositions for scent dispensers.

[0011] Of special interest are aroma chemicals which can impart one or more distinct sensory impressions to a composition, thereby contributing to a rich and interesting sensory profile, especially an olfactory profile of the composition. In this regard, aroma chemicals which can impart a floral violet note, fruity note, marine note, technical metallic note or any combination of two or more of these impressions are of major interest. In addition, the substantivity as well as the tenacity are of special interest in order to obtain a long-lasting odiferous impression in the composition as well as to the surface with which the composition is treated.

[0012] However, since even small changes in chemical structure bring about massive changes in the sensory properties such as odor and / or flavor, the targeted search for substances with certain and distinct sensory properties such as a certain odor is extremely difficult. The search for new aroma chemicals is therefore in most cases difficult and laborious without knowing whether a substance with the desired odor and / or flavor will even actually be found.

[0013] It is an object of the present invention to provide substances which can be used as an aroma chemical either alone or as mixtures in compositions; in particular odor-intensive substances having a pleasant odor are sought. Furthermore, they should be combinable with other aroma chemicals, allowing the creation of novel advantageous sensory profiles and their use in compositions.

[0014] It is an object of the present invention to provide new aroma chemicals which have a pleasant aroma, in particular a pleasant olfactory impression; preferably impressions selected from the group consisting of floral violet note, fruity note, marine note, technical metallic note and any combination of two or more of these notes.

[0015] 2-Octyl acetate is a component of the volatiles of Ecuadorian cocoa types Nacional and CCN51 (H. Rottiers et al., European Food Research and Technology, 2019, 245, 2459- 2478). Its odor is described by Rottiers et al. as earthy, herbal, humus, fruity. 2-Octyl acetate is also present in the headspace of green beers produced by the Saccharomyces cerevisiae yeast (I. Benucci et al., Food Chemistry, 2021, 340, 127900). Benucci et al. describe its odor similarly to Rottiers et al. as earthy, herbal, humus, undergrowth. Trained experts among the present inventors, who tested very pure 2-octyl acetate, characterize its scent as soapy, dusty, waxy, citrus (mandarine).

[0016] 2-Octyl acetate is principally attractive as aroma chemical, since apart from having the basic prerequisite for such a use, namely an aroma, especially an odor, it is readily available, both from petrochemical and bio-based sources.

[0017] M / BASFTR-2475-PC 230961W001

[0018] 3

[0019] While the above-described odor notes of 2-octyl acetate are interesting for some specific purposes, fresher, more natural, more citrus, and less soapy I waxy / earthy notes are more desirable, since they are suitable for a distinctly broader field of application.

[0020] A further object is thus to provide a compound which is able to boost or to modify the aroma of 2-octyl acetate so as to afford fresher, more natural citrus notes.

[0021] Another object of the present invention is to provide mixtures of aroma chemicals, to be more precise mixtures of 2-octyl acetate with another compound, which have a pleasant aroma impression, in particular a pleasant olfactory impression, more particularly a fresher and / or a more natural citrus aroma and / or a less soapy and / or a less waxy aroma, as compared to 2-octyl acetate when used alone.

[0022] In general, floral, fruity and marine notes are sought.

[0023] A further object of the present invention is that the aroma chemicals should be obtainable from readily available starting materials, allowing their fast and economic manufacturing.

[0024] SUMMARY OF THE INVENTION

[0025] Surprisingly, the objects of the present invention were achieved by oct-5-en-2-yl acetate and also by its mixtures with 2-octyl acetate.

[0026] It was surprisingly found that oct-5-en-2-yl acetate has a pleasant aroma, especially a pleasant olfactory impression; specifically an olfactory impression selected from floral violet note, fruity note, marine note, technical metallic note, or a combination of two or more of the afore-mentioned notes. Surprisingly, oct-5-en-2-yl acetate induces a pleasant aroma, especially a pleasant scent, even when used in very low concentrations.

[0027] It was moreover surprisingly found that mixtures of oct-5-en-2-yl acetate and 2-octyl acetate have a pleasant aroma, in particular a pleasant olfactory impression; especially a fresher aroma and / or a more natural citrus aroma and / or a less soapy aroma and / or a less waxy aroma, as compared to 2-octyl acetate alone. Surprisingly, this effect is achieved even when oct-5-en-2-yl acetate is used in very low concentrations, as compared to the concentration of 2-octyl acetate, even in concentrations far below 1% by weight, relative to the total weight of oct-5-en-2-yl acetate and 2-octyl acetate.

[0028] A first aspect of the present invention relates thus to oct-5-en-2-yl acetate of formula (I)

[0029] M / BASFTR-2475-PC 230961W001

[0030] 4 or a stereoisomer thereof or a mixture of different stereoisomers thereof.

[0031] A second aspect of the present invention relates to a mixture comprising the compound (I) or a stereoisomer thereof or a mixture of stereoisomers thereof, and 2-octyl acetate of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof.

[0032] A third aspect of the present invention relates to the use of the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, or of its above-defined mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, as an aroma chemical, preferably as a fragrance.

[0033] A further aspect of the present invention relates to the use of the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, or of its above-defined mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, for providing an aroma, preferably a fragrance, to a composition.

[0034] A further aspect of the present invention relates to a method of imparting an aroma impression to a composition comprising at least the step of adding the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, or its above-defined mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, to a composition (or mixing it with said composition); or comprising at least the step of mixing the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or its above-defined mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, simultaneously or sequentially with a part or with all other components of the targeted composition.

[0035] Another aspect of the present invention relates to the use of the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof for boosting or, preferably, modifying the aroma of the compound of formula (II) or of a stereoisomer thereof

[0036] M / BASFTR-2475-PC 230961W001

[0037] 5 or of a mixture of stereoisomers thereof, especially for rendering it fresher and / or more natural citrus and / or less soapy and / or less waxy, as compared to the aroma of the compound of formula (II).

[0038] Another aspect of the present invention relates to the use of the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, or of its mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof for boosting the aroma or for modifying the aroma character of a composition.

[0039] A further aspect of the present invention relates to a method of boosting the aroma of a composition, or to a method for modifying the aroma of a composition. Said method comprises at least the step of incorporating the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers or its mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof into a chemical composition, especially an aroma chemical composition, e.g. by mixing the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or its mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof with the composition the aroma of which is to be boosted or modified; or mixing the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or its mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof simultaneously or sequentially with a part or with all other ingredients of the targeted composition, such as, e.g., at least one other aroma chemical different from the compound of formula (I) and / or at least one non-aroma chemical carrier, so as to obtain the boosted or aroma-modified composition.

[0040] Furthermore, the compounds of formula (I) can be produced in good yields and purities by a simple synthesis starting from readily available starting materials. Thus, the compounds of the present invention can be produced in large scales and in a simple and cost-efficient manner.

[0041] DETAILED DESCRIPTION OF THE INVENTION

[0042] The following detailed description is merely exemplary in nature and is not intended to limit the present invention or the application and uses of the present invention. Furthermore, there is no intention to be bound by any theory presented in the preceding technical field, background, summary or the following detailed description.

[0043] Definitions

[0044] The terms “the invention relates to” and “the invention is directed to” are used synonymously throughout the invention.

[0045] M / BASFTR-2475-PC 230961W001

[0046] 6

[0047] The terms "comprising", "comprises" and "comprised of' as used herein are synonymous with "including", "includes" or "containing", "contains", and are inclusive or open-ended and do not exclude additional, non-recited members, elements or method steps. It will be appreciated that the terms "comprising", "comprises" and "comprised of' as used herein comprise the terms "consisting of', "consists" and "consists of".

[0048] Furthermore, the terms "(a)", "(b)", "(c)", "(d)" etc. and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the subject matter described herein are capable of operation in other sequences than described or illustrated herein. In case the terms “(A)”, “(B)” and “(C)” or AA), BB) and CC) or "(a)", "(b)", "(c)", "(d)", "(i)", "(ii)" etc. relate to steps of a method or use or assay there is no time or time interval coherence between the steps, that is, the steps may be carried out simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months or even years between such steps, unless otherwise indicated in the application as set forth herein above or below.

[0049] In the following passages, different aspects of the subject matter are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.

[0050] Reference throughout this specification to "one embodiment" or "an embodiment" or “preferred embodiment” means that a particular feature, structure or characteristic described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrases "in one embodiment" or "In a preferred embodiment" or “in a preferred embodiment” in various places throughout this specification are not necessarily all referring to the same embodiment but may refer. Furthermore, the features, structures or characteristics may be combined in any suitable manner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Furthermore, while some embodiments described herein include some, but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the subject matter, and form different embodiments, as would be understood by those in the art. For example, in the appended claims, any of the claimed embodiments are used in any combination.

[0051] Furthermore, the ranges defined throughout the specification include the end values as well, i.e. a range of 1 to 10 implies that both 1 and 10 are included in the range. For the avoidance of doubt, the applicant shall be entitled to any equivalents according to applicable law.

[0052] M / BASFTR-2475-PC 230961W001

[0053] 7

[0054] In the context of the present invention, the term "aroma" refers to a sensory property and comprises an odor and / or a flavor. Sensory property is related to the sensory perception of humans.

[0055] The term “aroma chemical” denotes a substance which is used to obtain a sensory or organoleptic (used interchangeably herein) impression and comprises its use to obtain an olfactory and / or a flavor impression. The term "olfactory impression" or “olfactory note” (used interchangeably here) denotes an odor impression without any positive or negative judgement, while the term “scent impression” or “fragrance impression” (used interchangeably herein) as used herein is connected to an odor impression which is generally felt as pleasant. Thus a “fragrance” or “scent” denotes an aroma chemical which predominately induces a pleasant odor impression. A flavor denotes an aroma chemical which induces a taste impression.

[0056] The term “aroma composition”, as used herein, refers to a composition which induces or has an aroma. The term aroma composition comprises “odor composition” and / or “flavor composition”. An odor composition is a composition which predominately induces an odor impression, and a flavor composition is a composition which predominantly induces a taste impression.

[0057] The term “aroma profile” denotes the overall aroma impression of an aroma chemical and is composed of the individual aroma impressions of an aroma chemical.

[0058] The term “odor composition” comprises “fragrance composition” or “scent composition” (used interchangeably herein), which predominately induce an odor impression which is generally felt as pleasant.

[0059] The general hedonistic expressions "advantageous sensory properties" or "advantageous organoleptic properties" describe the niceness and conciseness of an organoleptic impression conveyed by an aroma chemical. "Niceness" and "conciseness" are terms which are familiar to the person skilled in the art, such as a perfumer. Niceness generally refers to a spontaneously brought about, positively perceived, pleasant sensory impression. However, "nice" does not have to be synonymous with "sweet". "Nice" can also be the odor of musk or sandalwood. "Conciseness" generally refers to a spontaneously brought about sensory impression which - for the same test panel - brings about a reproducibly identical reminder of something specific. For example, a substance can have an odor which is spontaneously reminiscent of that of an "apple": the odor would then be concisely of "apples". If this apple odor were very pleasant because the odor is reminiscent, for example, of a sweet, fully ripe apple, the odor would be termed "nice". However, the odor of a typically tart apple can also be concise. If both reactions arise upon smelling the substance, in the example thus a nice and concise apple odor, then this substance has particularly advantageous sensory properties.

[0060] M / BASFTR-2475-PC 230961W001

[0061] 8

[0062] The expressions "combination of', "in combination with" or "combined with" when used herein referring to the compositions, methods or the use of two compounds, take account of the fact that the two compounds do not need to be used in the form of a physical mixture of said compounds but can be used (e.g., added) separately. Where the compounds are used separately, they can be used (e.g. added) sequentially (i.e. one after the other) in any order, or concurrently (i.e. basically at the same time).

[0063] The term “boosting”, or “boost” is used herein to describe the effect of enhancing and / or modifying the aroma of an aroma chemical or of a composition. The term “enhancing” comprises an improvement of the niceness and / or conciseness of an aroma and / or an improvement of the intensity. The term “modifying” comprises the change of an aroma profile. The terms “niceness” and “conciseness” are familiar to the person skilled in the art, such as a perfumer, and have the respective meaning.

[0064] The intensity can be determined via a threshold value determination. A threshold value of an odor is the concentration of a substance in the relevant gas space at which an odor impression can just still be perceived by a representative test panel, although it no longer has to be defined.

[0065] Booster effects are particularly desired in fragrance composition when top-note- characterized applications are required, in which the odor is to be conveyed particularly quickly and intensively, for example in deodorants, air fresheners or in the taste sector in chewing gums.

[0066] The term “tenacity” describes the evaporation behaviour over time of an aroma chemical. The tenacity can for example be determined by applying the aroma chemical to a test strip, and by subsequent olfactory evaluation of the odor impression of the test strip. For aroma chemicals with high tenacity the time span after which the panel can still identify an aroma impression is long.

[0067] The term “substantivity” describes the interaction of an aroma chemical with a surface, such as for example the skin or a textile, especially after subsequent treatment of the surface, such as for example washing. The substantivity can for example be determined by washing a textile with a textile detergent composition comprising the aroma chemical and subsequent olfactory evaluation of the textile directly after washing (wet textile) as well as evaluation of the dry textile after prolonged storage.

[0068] The term “stability” describes the behaviour of an aroma chemical upon contact with oxygen, light and / or other substances. An aroma chemical with high stability maintains its aroma profile over a long period in time, preferably in a large variety of compositions and under various storage conditions.

[0069] M / BASFTR-2475-PC 230961W001

[0070] 9

[0071] In order to impart a long-lasting aroma impression to a composition or to a surface treated with a composition, the tenacity, the substantivity as well as the stability of the aroma chemical in the compositions should preferably be high.

[0072] As used herein the terms “compound (I)” or “compound of formula (I)” refer to the compound of formula (I) including all the stereoisomeric forms (stereoisomers) thereof in all ratios. The same applies for the compound of formula (II).

[0073] The term “mixture” used herein denotes a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof.

[0074] The term "stereoisomer" is a general term used for all isomers of individual compounds that differ only in the arrangement of their atoms in space, not in the connectivity of the atoms Thus, the term stereoisomer includes mirror image isomers (enantiomers), geometric (cis / trans or Z / E) isomers, and diastereomers. For precise definitions of the terms, see G. Helmchen: "Vocabulary and Nomenclature of Organic Stereochemistry”. In Houben-Weyl E21a, Stereoselective Synthesis. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann (Hrsg.), 1995, 1-74. The possible isomers can be present as mixtures (i.e. racemates, cis / trans-m ixtures or mixtures of diasteroisomers).

[0075] In the present case, the compound (I), due to its C-C-double bond in the 5-position of the octenyl moiety, can be present as the pure Z (or cis) isomer (l-Z) or the pure E (or trans) isomer (l-E) or a mixture of the Z and the E-isomer in any mixing ratio. This is indicated by the crossed lines representing the C-C-double bond in formula (I).

[0076] The compound (I) contains moreover a stereogenic center at the 2-position of the octenyl radical, i.e. at that carbon atom of the octenyl radical which is bound to the oxygen atom. The compound can have pure S configuration or pure R configuration at this 2-position or can be a mixture of S- and R-configured compound (I) at this position in any ratio, including a 1 :1 (racemic) mixture.

[0077] M / BASFTR-2475-PC 230961W001

[0078] 10

[0079] The compound (II) contains a stereogenic center at the 2-position of the octyl radical, i.e. at that carbon atom of the octyl radical which is bound to the oxygen atom. The compound can be the pure S enantiomer or the pure R enantiomer or the racemic mixture or any non- racemic mixture thereof.

[0080] In terms of the present invention, the term "pure enantiomer" (or pure configuration) is understood as a non-racemic mixture of a specific compound, where the designated enantiomer (or configuration) is present in an enantiomeric excess of > 90 %ee.

[0081] In terms of the present invention, the term "pure diastereomer" (e.g. pure E or pure Z isomer) is understood as the designated diastereomer which is present in an amount of > 90 %, based on the total amount of diastereomers of said compound.

[0082] In the present context, the term “oct-5-en-2-yl acetate” I "compound (I)" or “2-octyl acetate” I "compound (II)", when not defined as a specific stereoisomer or a specific mixture of stereoisomers, refers to the form of the compound as it is obtained in a non-stereoselective method used for its production. The term is however also used if it is not necessary or not possible to specify in more detail the stereochemistry of the compound (I) or (II).

[0083] Embodiments (E.x) of the invention

[0084] General and preferred embodiments E.x are summarized in the following, non-exhaustive list. Further preferred embodiments become apparent from the paragraphs following this list.

[0085] E.1. A compound of formula or a stereoisomer thereof or mixture of stereoisomers thereof.

[0086] E.2. The compound according to embodiment E.1 , which is present as the Z isomer.

[0087] E.3. The compound according to embodiment E.1 , which is present as a mixture of the Z and the E isomer, wherein the Z isomer is present in an amount of >50%, relative to the total amount of the E and the Z isomer.

[0088] E.4. The compound according to embodiment E.3, wherein the Z isomer is present in an amount of at least 80%, relative to the total amount of the E and the Z isomer.

[0089] E.5. The compound according to embodiment E.4, wherein the Z isomer is present in an amount of at least 90%, relative to the total amount of the E and the Z isomer.

[0090] E.6. The compound according to embodiment E.5, wherein the Z isomer is present in an amount of at least 93%, relative to the total amount of the E and the Z isomer.

[0091] M / BASFTR-2475-PC 230961W001

[0092] 11

[0093] E.7. The compound according to embodiment E.6, wherein the Z isomer is present in an amount of at least 95%, relative to the total amount of the E and the Z isomer.

[0094] E.8. The compound according to embodiment E.5, wherein the Z isomer is present in an amount of from 92 to 98%, relative to the total amount of the E and the Z isomer.

[0095] E.9. A mixture comprising

[0096] - the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof according to any of embodiments E.1 to E.8; and

[0097] - the compound of formula (II) or a stereoisomer thereof or a mixture of stereoisomers thereof.

[0098] E.10. The mixture according to embodiment E.9, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1:10000 to 10000:1.

[0099] E.11. The mixture according to embodiment E.10, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1 : 10000 to 1 : 10.

[0100] E.12. The mixture according to embodiment E.11, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1 :2000 to 1 :40.

[0101] E.13. The mixture according to embodiment E.12, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1:1000 to 1:50.

[0102] E.14. The mixture according to embodiment E.13, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1 :500 to 1 :90.

[0103] E.15. The mixture according to embodiment E.14, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1 :450 to 1 :95.

[0104] E.16. Use of the compound of formula (I) or of a stereoisomer thereof or of a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, for boosting or modifying the aroma of the compound of formula (II) as defined in embodiment E.9.

[0105] M / BASFTR-2475-PC 230961W001

[0106] 12

[0107] E.17. Use of the compound of formula (I) or of a stereoisomer thereof or of a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or of the mixture as defined in any of embodiments E.9 to E.15, as an aroma chemical or to impart an aroma impression to a composition.

[0108] E.18. The use according to embodiment E.17, as a fragrance or to impart a fragrance to a composition.

[0109] E.19. A method of imparting an aroma impression to a composition, comprising at least the step of adding the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, to a composition; or comprising mixing simultaneously or consecutively the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, with the other components of said composition or with pre-formed mixtures of a part of the other components of said composition.

[0110] E.20. The use or method according to embodiments E.17 to E.19, wherein in case that the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.9 is used, the aroma impression is selected from the group consisting of floral violet note, fruity note, marine note, technical metallic note and any combination of two or more of these notes.

[0111] E.21. The use or method according any of the embodiments E.17 to E.20, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.001 to 99.9% by weight, based on the total weight of the composition.

[0112] E.22. The use or method according to embodiment E.21 , wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.005 to 90% by weight, based on the total weight of the composition.

[0113] E.23. The use or method according to embodiment E.22, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 80% by weight, based on the total weight of the composition.

[0114] E.24. The use or method according to embodiment E.23, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 60% by weight, based on the total weight of the composition.

[0115] E.25. The use or method according to embodiment E.24, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of

[0116] M / BASFTR-2475-PC 230961W001

[0117] 13 embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 40% by weight, based on the total weight of the composition.

[0118] E.26. The use or method according to embodiment E.25, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 10% by weight, based on the total weight of the composition.

[0119] E.27. The use or method according to embodiment E.26, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 7% by weight, based on the total weight of the composition.

[0120] E.28. The use or method according to embodiment E.27, wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15 is present in the composition in a total amount in the range of from 0.01 to 6% by weight, based on the total weight of the composition.

[0121] E.29. A composition comprising the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or a mixture as defined in any of embodiments E.9 to E.15, and

[0122] (i) at least one aroma chemical (X) other than compounds of formula (I) and (II) or

[0123] (ii) at least one non-aroma chemical carrier, or

[0124] (iii) both of (i) and (ii).

[0125] E.30. The composition according to embodiment E.29, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.001 to 99.9% by weight, based on the total weight of the composition.

[0126] E.31. The composition according to embodiment E.30, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.005 to 90% by weight, based on the total weight of the composition.

[0127] E.32. The composition according to embodiment E.31, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.01 to 80% by weight, based on the total weight of the composition.

[0128] E.33. The composition according to embodiment E.32, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15,

[0129] M / BASFTR-2475-PC 230961W001

[0130] 14 is present in a total amount in the range of from 0.01 to 60% by weight, based on the total weight of the composition.

[0131] E.34. The composition according to embodiment E.33, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.01 to 40% by weight, based on the total weight of the composition.

[0132] E.35. The composition according to embodiment E.34, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.01 to 10% by weight, based on the total weight of the composition.

[0133] E.36. The composition according to embodiment E.35, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.01 to 7% by weight, based on the total weight of the composition.

[0134] E.37. The composition according to embodiment E.36, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of embodiments E.1 to E.8, or the mixture as defined in any of embodiments E.9 to E.15, is present in a total amount in the range of from 0.01 to 6% by weight, based on the total weight of the composition.

[0135] E.38. The composition according to any of embodiments E.29 to E.37, wherein the at least one non-aroma chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant-active agents, or solvents.

[0136] E.39. The composition according to any of embodiments E.29 to E.38, comprising at least one aroma chemical (X) different from the compounds of formula (I) and (II) and optionally at least one non-aroma chemical carrier, where the at least one aroma chemical (X) different from the compounds of formula (I) and (II) is selected from the group consisting of: 2,6,10-trimethyl-9-undecenal (Adoxal), 3a,4,5,6,7,7a-hexahydro-1 H-4,7- methanoinden-6-yl acetate (verdyl acetate), dodecanal (aldehyde C-12 (lauric)), 2- methylundecanal (aldehyde C12 MNA), aldehyde C-14 (gamma-undecalactone; 1 ,4- undecanolide), cyclamen aldehyde (2-methyl-3-(4-isobutylphenyl)-propanal), ambrocenide ((4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4h-4a,9- methanoazuleno(5,6-d)-1 ,3-dioxole), benzyl acetate, beta-ionone, isoamyl butyrate, calone (calone 1951 , watermelon ketone, 7-methylbenzo[b][1 ,4]dioxepin-3-one), cetalox (naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-), cis-3-hexenyl isobutyrate, corps cassis, dartanol (also known as bacdanol, sandolene, topanzol or 2- ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), dupical (4-(octahydro-4,7- methano-5H-inden-5-ylidene)butanal), ethyl maltol (2 ethyl-3-hydroxy-4H-pyran-4- one), ethyl vanillin (4-hydroxy-3-ethoxybenzaldehyde), floralozone (florone, florazon, 3-

[0137] M / BASFTR-2475-PC 230961W001

[0138] 15

[0139] (4-ethylphenyl)-2,2-dimethylpropanal), galbascone (dynascone; 1-(5,5-dimethyl-1 cyclo-,hexen-1-yl)-4-penten-1-one), gamma-decalactone (1,4-decanolide), gammaoctalactone (4-octanolide), geranyl acetate, habanolide (trans- 11-pentadecen- 1,15- olide; cis and trans-12-pentadecen-1, 15-olide), allyl heptanoate, hexyl acetate, indol, Iso E Super, isobutyl quinoleine, isoeugenol, javanol, lemonile, limette distillee, manzanate (ethyl 2-methylpentanoate), delta-muscenone, oxane, peonile, prenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl salicylate, isoamyl salicylate, stemone, tetrahdrolinalool, triplal (ligustral; vertocitral; trivertal; 2,4-dimethyl-3- cyclohexenecarbox-aldehyde), undecavertol (4-methyl-3-decen-5-ol), verdox (OTBCH, 2-tert-butylcyclohexyl acetate), violettyne (1,3-undecadien-5-yne), allyl 3- cyclohexylpropionate, allyl heptylate, ambroxide (ambrox; ambroxan; 3a, 6, 6, 9a tetramethyldodecahydronaphtho-,[2,1-b]furan), bacdanol (topanzol; sandolen; 2-ethyl- 4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), citronellyl acetate, cyclopentadecanolide (15-pentadecanolacton), damascenone, dihydromyrcenol, dimethyl benzyl carbinyl butyrate (alpha, alpha-dimethylphenylethyl butyrate), ethyl butyrate, ethyl maltol, ethyl 2-methylbutyrate, evernyl (methyl 2,4-dihydroxy-3,6- dimethylbenzoate), fructalate, hedione, hexyl isobutyrate, isoamyl acetate, methyl benzoate, methyl propyl oxathiane, para-cresyl methyl ether, phenoxyethyl isobutyrate, phenylethyl alcohol, pyranol (florol; 2-isobutyl-4-methyltetrahydro-2H pyran-4-ol), verdyl propionate (3a,4,5,6,7,7a-hexahydro-4,7-methano-1 H-inden-5(6)-yl propionate), 8-mercapto-menthanone, aldehyde C-18 (gamma-nonalactone; 5-pentyloxolan-2-one), alpha-ionone, citronellyl nitrile, cyclabute (tricyclodecenyl isobutyrate; 3a, 4, 5, 6, 7,7a- hexahydro-4,7-methano-1 H-inden-5(6)-yl isobutyrate), alpha-damascone, helvetolide, hexyl salicylate, hydratropic aldehyde dimethyl acetal (2-phenylpropionaldehyde dimethyl acetal), limonene, linalyl acetate, melonal, orange oil, para-menthenethiol, styrallyl acetate (1 -phenylethyl acetate), terpenyl acetate, hydroxycitronellal, amylvinylcarbinol (1-octen-3-ol), camphor, ethyl linalool, eucalyptol (cineol), hexyl butyrate, hexyl caproate (hexyl hexanoate), isoborneol, linalool oxide (2-(5-methyl-5- vinyltetrahydro-1-furyl)-2-propanol), methyl hexyl ketone (2-octanone), methyl octalactone (whisky lactone, 3-methyl-4-octanolide, 3-methyl-1, 4-octanolide, 5-butyl-4- methyloxolan-2-one), ocimene, octyl acetate, terpineol alpha, terpinolene, terpinly acetate, para-cymene (1-methyl-4-(propan-2-yl)benzene, 4-isopropyltoluene) and mixtures thereof.

[0140] E.40. The composition according to any of the embodiments E.29 to E.39, wherein the composition is selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

[0141] E.41. A process for synthesizing the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof as defined in any of embodiments E.1 to E.8, comprising at least the steps of a) acetylation of a compound of formula (III)

[0142] M / BASFTR-2475-PC 230961W001 to form the compound of formula (I), and b) optionally purifying the compound of formula (I) obtained in step a).

[0143] Compound (I)

[0144] One embodiment of the present invention is directed to the compound of formula (I) (oct- 5- en-2-yl acetate) or a stereoisomer thereof or a mixture of different stereoisomers thereof.

[0145] As explained above, the crossed lines representing the C-C double bond indicate that the compound (I) can be present as the Z isomer, as the E isomer or as a mixture of the Z and the E isomer.

[0146] Preference is given to the Z isomer or a mixture of Z and E isomer, where the Z isomer predominates, i.e. where it is present in an amount of >50%, relative to the total amount of E and Z isomer. In such a mixture, the Z isomer is preferably present in an amount of at least 80%, more preferably at least 90%, in particular at least 93%, specifically at least 95%, relative to the total amount of E and Z isomer. In an alternatively preferred embodiment, in such a mixture, the Z isomer is preferably present in an amount of 92 to 98%, relative to the total amount of E and Z isomer. According to the above definition, mixtures wherein the Z isomer is present in >90%, relative to the total amount of E and Z isomer, are considered as “pure” Z isomer in terms of the present invention.

[0147] Compound (I) is, for example, available via acetylation of the corresponding alcohol oct- 5- en-2-ol of formula (III); see below.

[0148] M / BASFTR-2475-PC 230961W001

[0149] 17

[0150] The invention relates thus also to a process for synthesizing the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, comprising at least the steps of a) acetylation of a compound of formula (III) to form the compound of formula (I), and b) optionally purifying the compound of formula (I) obtained in step a).

[0151] Acetylation [i.e. esterification of an alcohol - here compound (III) - to form an acetic acid ester - here compound (I)] can be carried out by known means, such as reacting the alcohol (III) with acetic acid or with a more active derivative thereof, such as an acetic acid halide (e.g. the chloride or bromide), acetic anhydride or an active ester of acetic acid under typical esterification conditions, if desired under removal of the reaction water formed (if the acid as such is used) or of the acid formed (if the anhydride is used) to enhance the reaction rate, or under neutralization (if an acetic acid halide is used).

[0152] The esterification can be carried out in the presence of an esterification catalyst; this is especially indicated if acetic acid as such is used. Suitable esterification catalysts are well known in the art and are for example metal based catalysts, e.g. 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, e.g. mineral acids, such as sulfuric acid, hydrochloric acid or phosphoric acid; organic sulfonic acids, such as methane sulfonic acid or para-toluene sulfonic acid or strongly acidic cation exchange resins.

[0153] The term "strongly acidic cationic exchanger" refers to a cationic exchanger in the H+form which has strongly acidic groups. The strongly acidic groups are generally sulfonic acid groups; they are generally bonded to a polymer matrix, which can be e.g. gel-like and / or macroporous. Preference is given to styrene (co)polymers containing sulfonic acid groups, specifically to styrene-divinyl benzene copolymers containing sul-fonic acid groups. Commercial examples for such cationic 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 Nation® NR-50.

[0154] M / BASFTR-2475-PC 230961W001

[0155] 18

[0156] Alternatively, the cation exchanger can be a perfluorinated ion exchange resin, sold e.g. under the Nation® brand of DuPont.

[0157] The esterification can be carried out in the presence of a base; this is especially indicated if an acetic acid halide is used. Suitable bases are for example organic bases, such as tertiary amines, e.g. trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine and the like, or basic N-heterocycles, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.

[0158] The alcohol (III) is typically reacted with at least one equivalent of the acylating agent.

[0159] The reaction can be carried out in a solvent or neat.

[0160] After completion of the reaction, the esterification product can be isolated by usual means, if necessary after neutralization (especially if an acetic acid halide or acetic anhydride was used as starting material or if the acid was used in excess) and / or removal of the catalyst (especially if this is solid, e.g. one of the above-mentioned metal based catalysts or ionic exchange resins), for example by distillative, extractive or chromatographic methods. If desired, the isolated product can subsequently be further purified.

[0161] Z- and E-isomers can be prepared by subjecting the compound (I), if this is present as a mixture of its Z and E isomer, to a suitable separation method, such as chromatographic or distillative separation.

[0162] Alternatively, since the above acetylation conditions are generally not as harsh as to promote the conversion of the one geometric isomer into the other, essentially pure Z or E isomers can be prepared by starting from the alcohol (III) in the essentially pure Z or E form.

[0163] The alcohol (III) is either commercially available or can be prepared, for example, by subjecting hept-4-enal to a Grignard reaction with a methyl Grignard reagent, such as methylmagnesium bromide (CHsMgBr). Suitable conditions for the Grignard reaction are well-known, such as the use of diethyl ether or tetra hydrofuran or another ether as solvent under anhydrous conditions.

[0164] Since the Grignard reaction does not essentially promote the conversion of the one geometric isomer into the other, essentially pure Z or E isomers of the alcohol (III) can be obtained by starting from essentially pure Z- or E-hept-4-enal.

[0165] Mixtures

[0166] In another embodiment, the present invention relates to a mixture comprising the compound of formula (I)

[0167] M / BASFTR-2475-PC 230961W001

[0168] 19 or a stereoisomer thereof or a mixture of different stereoisomers thereof, and the compound of formula (II) (2-octyl acetate) or a stereoisomer thereof or a mixture of different stereoisomers thereof.

[0169] Again, preference is given to the compound (I) being present in form of the Z isomer or of a mixture of Z and E isomer, where the Z isomer predominates, i.e. where it is present in an amount of >50%, relative to the total amount of E and Z isomer. In such a mixture, the Z isomer is preferably present in an amount of at least 80%, more preferably at least 90%, in particular at least 93%, e.g. at least 95%, or from 92 to 98%, relative to the total amount of E and Z isomer.

[0170] Compounds (II) are commercially available or can be obtained by standard methods known to those skilled in the art, such as Grignard reaction of heptanal with a methyl Grignard reagent, such as methylmagnesium bromide (CHsMgBr). Suitable conditions for the Grignard reaction are well-known, such as the use of diethyl ether or tetrahydrofuran or another ether as solvent under anhydrous conditions.

[0171] To obtain a specific enantiomer of the compound (II) [(2S)-2-octyl acetate or (2R)-2-octyl acetate] or an enantiomer mixture in which one of the enantiomers is enriched, the racemic compound (II) can be subjected to a suitable resolution method, such as chiral chromatography, e.g. preparative HPLC with a chiral column.

[0172] In an embodiment of the present invention, the mixture comprises the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof in a weight ratio in the range of 1:10000 to 10000:1 , preferably from 1:10000 to 1:10, more preferably from 1:2000 to 1:40, even more preferably from 1:1000 to 1 :50, particularly preferably from 1:500 to 1 :90, specifically from 1:450 to 1:95.

[0173] M / BASFTR-2475-PC 230961W001

[0174] 20

[0175] In an alternatively preferred embodiment of the present invention, the mixture comprises the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof in an amount of 0.01 to 10% by weight, more preferably 0.05 to 2.5% by weight, even more preferably 0.1 to 2% by weight, particularly preferably 0.15 to 1.5% by weight, specifically 0.2 to 1.5% by weight, e.g. 0.2 to 1 % by weight or 0.2 to 0.5% by weight, relative to the total weight of the compound (I) and the compound of formula (II).

[0176] The mixtures can for example be obtained by mixing compounds (I) and (II) in the desired ratio.

[0177] Use of compounds of formula (I)

[0178] In one embodiment, the present invention is direct to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof as an aroma chemical, preferably as a fragrance.

[0179] In another embodiment, the present invention is direct to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof to impart an aroma, preferably a fragrance, to a composition.

[0180] A specific embodiment of the present invention is direct to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof as aroma chemical (preferably as a fragrance) with a floral violet note, fruity note, marine note, technical metallic note or any combination of two or more of these notes; or to impart a floral violet note, fruity note, marine note, technical metallic note or any combination of two or more of these notes to a composition.

[0181] Another embodiment of the present invention is directed to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof in admixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof as an aroma chemical, preferably as a fragrance.

[0182] In a further embodiment the present invention is directed to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof or its mixture with the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof to boost the aroma of a composition.

[0183] In an embodiment of the present invention, the compound (I) or its mixture with the compound of formula (II) is used as a fragrance or to confer a fragrance to a composition.

[0184] In a further embodiment, the present invention is directed to the use of the compound (I) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof to boost or modify

[0185] M / BASFTR-2475-PC 230961W001

[0186] 21 the aroma, preferably the fragrance, of the compound of formula (II) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof.

[0187] In particular, the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof is used to render the aroma, preferably the fragrance, of the compound (II) or of a stereoisomer thereof or of a mixture of different stereoisomers thereof less soapy and / or less dusty and / or less waxy and / or fresher and / or more natural and / or more citrus.

[0188] Preferably, compound (I) is used to impart a combination of two or more of the impression which are selected from the group consisting of floral violet note, fruity note, marine note, technical metallic note to a composition.

[0189] Suitable compositions as described above are for example compositions used in personal care, in home care, in industrial applications as well as compositions used in other applications, such as pharmaceutical compositions or crop protection compositions.

[0190] Preferably, the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or its mixture with compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof according to the present invention are used in a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0191] The compositions are described in more detail in the below paragraphs.

[0192] Composition

[0193] The present invention relates moreover to a composition comprising the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and

[0194] (i) at least one aroma chemical (X) different from the compound (I), or

[0195] (ii) at least one non-aroma chemical carrier, or

[0196] (iii) both of (i) and (ii).

[0197] Preferably the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof in a total amount in the range from 0.001 to 99.9% by weight, preferably from 0.005 to 90% by weight, more preferably from 0.01 to 80%, in particular from 0.01 to 60% by weight, more particularly from 0.01 to 40% by weight, e.g. from 0.01 to 10% by weight or 0.01 to 5% by weight, based on the total weight of the

[0198] M / BASFTR-2475-PC 230961W001

[0199] 22 composition. These amounts of compound (I) apply especially if the composition does not comprise compound (II), i.e. if compound (I) is not used in admixture with compound (II).

[0200] In another preferred embodiment of the invention, the compositions comprise the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof in an overall amount of from 0.001 to 10 weight-%, preferably from 0.005 to 5 weight-%, in particular from 0.01 to 4 weight-%, e.g. from 0.01 to 3 weight-%, based on the total weight of the composition. These amounts of compound (I), too, apply in this context especially if the composition does not comprise compound (II).

[0201] Another embodiment of the present invention relates to a composition comprising

[0202] (i) a mixture of the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and

[0203] (ii) at least one aroma chemical (X) other than compound (I) and (II), or

[0204] (iii) at least one non-aroma chemical carrier, or

[0205] (iv) both of (ii) and (iii).

[0206] Preferably the composition comprises the mixture (i) of compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, i.e. the compounds (I) and (II) or their stereoisomers or stereoisomer mixtures, in a total amount in the range from 0.001 to 99.9% by weight, preferably from 0.005 to 90% by weight, more preferably from 0.01 to 80%, in particular from 0.01 to 60% by weight, more particularly from 0.01 to 40% by weight, specifically from 0.01 to 10% by weight, e.g. 0.01 to 7% by weight or 0.01 to 5% by weight, based on the total weight of the composition.

[0207] In another preferred embodiment of the invention, the compositions comprise the mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof in an overall amount of from 0.001 to 10 weight-%, preferably from 0.005 to 5 weight-%, in particular from 0.01 to 4 weight-%, e.g. from 0.01 to 3 weight-%, based on the total weight of the composition.

[0208] Preferably, the composition is an aroma composition, more preferably a fragrance composition

[0209] Aroma chemical different from the compounds of formula (I) and compounds of formula (II):

[0210] In one embodiment, the composition comprises at least one aroma chemical which is different from the compounds of formula (I) (and (II), where applicable). Aroma chemicals

[0211] M / BASFTR-2475-PC 230961W001

[0212] 23 which are different from the compounds of formula (I) and from the compounds of formula (II) are also referred to as aroma chemical (X).

[0213] By virtue of their physical properties, the compounds of formula (I) (and (II), where applicable) are well combinable with aroma chemicals which are different from the compounds of formula (I) [and (II)] and other customary ingredients in aroma compositions, in particular fragrance compositions. This allows, e.g., the creation of aroma compositions (preferably fragrance compositions) which have novel advantageous sensory profiles. Especially, as already explained above, the compounds can provide a booster effect for other aroma chemicals (such as fragrances).

[0214] The aroma chemical (X) is preferably selected from the group consisting of: geranyl acetate, alpha-hexylcinnamaldehyde, 2 phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate , 4, 6, 6, 7, 8, 8 hexamethyl-1 ,3,4,6,7,8-hexa- hydro-,cyclopenta[g]benzopyran, tetrahydrolinalool, ethyllinalool, benzyl salicylate, 2 methyl- 3-(4-tert-butylphenyl)propanal, 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, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl 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, hexyl salicylate, 4 tert-butylcyclohexyl acetate, 2-tert- butylcyclohexyl acetate, alpha-ionone, n alpha-methylionone, alpha-iso-methylionone, coumarin, terpinyl acetate, 2 phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3- cyclohexene-carboxaldehyde, alpha-amylcinnamaldehyde, ethylene brassylate, (E) and / or (Z)-3-methylcyclopentadec-5 enone, 15-pentadec-11-enolide and / or 15-pentadec-12- enolide, 15-cyclo-,pentadecanolide, 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, 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 and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.

[0215] In a preferred embodiment, the at least one aroma chemical (i) is selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4- methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and methyl benzoate.

[0216] M / BASFTR-2475-PC 230961W001

[0217] 24

[0218] In another preferred embodiment, the at least one aroma chemical (i) is selected from the group consisting of ethylvanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) and 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0219] Further aroma chemicals with which the compound of formula can be combined to give a composition according to the present invention can be found, e.g., in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N. J., 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th Ed., Wiley- VCH, Weinheim 2001. Specifically, mention may be made of: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as e.g. ambergris tincture; amyris oil; angelica seed oil; angelica root oil; aniseed oil; valerian oil; basil oil; tree moss absolute; bay oil; mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calmus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassia absolute; castoreum absolute; cedar leaf oil; cedar wood 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; oak moss 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; gurjun balsam; gurjun balsam oil; helichrysum absolute; helichrysum oil; ginger oil; iris root absolute; iris root oil; jasmine absolute; calmus oil; camomile oil blue; roman camomile 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; lime oil distilled; lime oil pressed; linalool oil; litsea cubeba oil; laurel leaf oil; mace oil; marjoram oil; mandarin oil; massoia bark oil; mimosa absolute; musk seed oil; musk tincture; clary sage oil; nutmeg oil; myrrh absolute; myrrh oil; myrtle oil; clove leaf oil; clove flower oil; neroli oil; olibanum absolute; olibanum oil; opopanax oil; orange blossom absolute; orange oil; origanum oil; palmarosa oil; patchouli oil; perilla oil; peru balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil; peppermint oil; pepper oil; pimento oil; pine oil; pennyroyal oil; rose absolute; rose wood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spike-lavender oil; star anise oil; styrax oil; tagetes oil; fir needle oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; wine lees oil; wormwood oil; winter green oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof, or ingredients isolated therefrom; individual fragrances from the group of hydrocarbons, such as e.g. 3 carene; alpha-pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p-cymene; bisabolene; camphene;

[0220] M / BASFTR-2475-PC 230961W001

[0221] 25 caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene;

[0222] (E,Z)-1 ,3,5-undecatriene; styrene; diphenylmethane; the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2- methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 1-octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-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; the aliphatic aldehydes and acetals thereof such as e.g. 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; heptanal diethylacetal; 1 ,1- dimethoxy-2,2,5 trimethyl-4-hexene; citronellyloxyacetaldehyde; (E / Z)-1-(1- methoxypropoxy)-hex-3-ene; the aliphatic ketones and oximes thereof such as e.g. 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; the aliphatic sulfur-containing compounds such as e.g. 3-methylthiohexanol; 3- methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol; the aliphatic nitriles such as e.g. 2-nonenenitrile; 2-undecenenitrile; 2 tridecenenitrile; 3,12- tridecadienenitrile; 3,7-dimethyl-2,6-octadienenitrile; 3,7-dimethyl-6 octenenitrile; the esters of aliphatic carboxylic acids such as e.g. (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-octinate; methyl 2-noninate; allyl 2- isoamyloxy acetate; methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate; the acyclic terpene alcohols such as e.g. 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; 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 the formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2 butenoates thereof;

[0223] M / BASFTR-2475-PC 230961W001

[0224] 26 the acyclic terpene aldehydes and ketones such as e.g. geranial; neral; citronellal; 7 hydroxy-3, 7-dimethyloctanal; 7 methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9 undecenal; geranyl acetone; as well as the dimethyl and diethylacetals of geranial, neral, 7-hydroxy-3,7- dimethyloctanal; the cyclic terpene alcohols such as e.g. menthol; isopulegol; alphaterpineol; terpine-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guajol; and the formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates thereof; the cyclic terpene aldehydes and ketones such as e.g. menthone; isomenthone; 8 mercaptomenthan-3-one; carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n- methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alphairone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma- 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-,naphthalene-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1- cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal; beta-sinensal; acetylated cedar wood oil (methyl cedryl ketone); the cyclic alcohols such as e.g. 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; the cycloaliphatic alcohols such as e.g. alpha-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; the cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; cyclododecyl methyl ether; 1 ,1 -dimethoxycyclododecane; (ethoxymethoxy)cyclo-dodecane; alpha-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; the cyclic and macrocyclic ketones such as e.g. 4-tert-butylcyclohexanone; 2,2,5 trimethyl-5- pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclo-pentanone; 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-cyclopenta-decenone; 3-methyl-5- cyclopentadecenone; 3-methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-

[0225] M / BASFTR-2475-PC 230961W001

[0226] 27 tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7- dihydro-1 ,1 ,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclo-hexadecen-1-one; 7- cyclohexadecen-1-one; (7 / 8)-cyclohexadecen-1-one; 9 cyclo-heptadecen-1-one; cyclopentadecanone; cyclohexadecanone; the cycloaliphatic aldehydes such as e.g. 2,4-dimethyl-3-cyclohexenecarbaldehyde; 2 methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3 cyclohexene carbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde; the cycloaliphatic ketones such as e.g. 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 cyclo-hexen-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; the esters of cyclic alcohols such as e.g. 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; the esters of cycloaliphatic alcohols such as e.g. 1 -cyclohexylethyl crotonate; the esters of cycloaliphatic carboxylic acids such as e.g. 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 cyclohexene-carboxylate; ethyl 2- methyl-1 ,3-dioxolane-2-acetate; the araliphatic alcohols such as e.g. 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; the esters of araliphatic alcohols and aliphatic carboxylic acids such as e.g. benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2- phenylethyl propionate; 2-phenylethyl isobutyrate; 2 phenylethyl isovalerate; 1 phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate;

[0227] M / BASFTR-2475-PC 230961W001

[0228] 28 alpha, alpha-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4- methoxybenzyl acetate; the araliphatic ethers such as e.g. 2-phenylethyl methyl ether; 2 phenylethyl isoamyl ether;

[0229] 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1 ,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1 ,2-d]-m-dioxine; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1 ,2-d]-m dioxine; the aromatic and araliphatic aldehydes such as e.g. benzaldehyde; phenylacetaldehyde; 3- phenylpropanal; hydratropaaldehyde; 4-methylbenzaldehyde; 4 methylphenylacetaldehyde;

[0230] 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; alpha-butylcinnamaldehyde; alpha- amylcinnamaldehyde; alpha-hexylcinnamaldehyde; 3 methyl-5-phenylpentanal; 4- methoxybenzaldehyde; 4-hydroxy-3 methoxy-benzaldehyde; 4-hydroxy-3- ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2- methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal; the aromatic and araliphatic ketones such as e.g. acetophenone; 4-methylacetophenone; 4- methoxyacetophenone; 4-tert-butyl-2,6-dimethylaceto-phenone; 4-phenyl-2-butanone; 4-(4- hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)-ethanone; 2-benzofuranylethanone; (3- methyl-2-benzofuranyl)ethanone; benzophenone; 1 ,1 ,2,3,3,6-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)-1 H-5 indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2- acetonaphthone; the aromatic and aliphatic carboxylic acids and esters thereof such as e.g. benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; 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; the nitrogen-containing aromatic compounds such as e.g. 2,4,6-trinitro-1 ,3-dimethyl-5 tertbutylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamonitrile; 3 methyl-5- phenyl-2-pentenonitrile; 3-methyl-5-phenylpentanonitrile; methyl anthranilate; methyl-N- methylanthranilate; 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 isopropyl-pyrazine; 2-isobutyl-3-methoxypyrazine;

[0231] M / BASFTR-2475-PC 230961W001

[0232] 29 the phenols, phenyl ethers and phenyl esters such as e.g. estragole; anethole; eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1 ,4- dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2 ethoxy-5-(1 -propenyl) phenol; p-cresyl phenylacetate; the heterocyclic compounds such as e.g. 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; the lactones such as e.g. 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- pentadecen- 1 ,15-olide; cis and trans-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; octa-hydrocoumarin.

[0233] Further aroma chemicals with which the compound of formula can be combined to give a composition according to the present invention are allyl ionone, Tamarine base, amyl butyrate, ethyl-2-methyl butyrate, Helvetolide, Fructalate, hexyl isobutyrate, methyl propyl oxathione, para-cresyl methylether, citronellyl nitrile, terpinolene, tetrahydro mugol, nopyl acetate, allyl amyl glycolate, ambrocenide, Rhubafuran 2-methylbutyric acid, citral, safranal, nironal (dodeca-4,8,11-trienal), cis-6-nonenol trans-2-cis-6-nonadienal, Violettyne, butyrate- cis-3-hexenyle, orange terpenes, lemonile, Liffarome, Amber Xtreme, dihydro rose oxide styrallyl propionate, peonile, cassis base, amyl salicylate, polysantol, aldehyde C12 MNA, neopentylglycol diacetate, Javanol, Cyclomyral, Floral Super, cyclomethylene citronellol, isobornyl acetate, pyranyl acetate, Hedione, hexyl caproate (hexyl hexanoate).

[0234] The aroma chemical (X) used in the composition are obtained from known commercial sources and as a rule procured from Germany.

[0235] In a preferred embodiment, the composition comprises at least one compound of formula (I) and at least one aroma chemical (X).

[0236] In another preferred embodiment, the composition comprises at least one compound of formula (I), at least one compound of formula (II) and at least one aroma chemical (X).

[0237] In a specific embodiment, the aroma chemical (X) is selected from the group consisting of: geranyl acetate, alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably with a content of cis isomer of more than 60 wt.%),

[0238] M / BASFTR-2475-PC 230961W001

[0239] 30

[0240] 4, 6, 6, 7, 8, 8 hexamethyl-1 ,3,4,6,7,8-hexa-,hydro-'cyclopenta[g]-benzopyran, linalool, tetrahydrolinalool, ethyllinalool, benzyl salicylate, 2 methyl-3-(4-tert-butylphenyl)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, citronellyl acetate, citronellol, geraniol, 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-tetramethyhnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclo_'hexyl acetate, alpha-ionone, n- alpha-methylionone, alpha-iso-rnethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, alpha- amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadec-5-enone, (Z)-3- methylcyclo-'penta-'dec-5-enone, 15-pentadec- 11 -enolide, 15-pentadec-12-enolide, 15- cyclo-'pentadecanolide, 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-cyclohexenecarbox-alde-,hyde, 2, 4,4,7- tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3- isopropylphenyl)butanal, citral, citronellal, 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 content of cis isomers of 70 wt.% 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-butyl-cyclo_'hexyl) acetate, 3-[5,5,6- trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, beta-ionone, beta-n-methylionone, beta-isomethylionone, alpha-irone, alpha-damascone, beta-damascone, beta-damascenone, delta-damascone, acetylated cedar wood oil, and mixtures thereof.

[0241] In another specific embodiment, the aroma chemical (X) is selected from the group consisting of:

[0242] 2,6,10-trimethyl-9-undecenal (Adoxal), 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl acetate (verdyl acetate), dodecanal (aldehyde C-12 (lauric)), 2-methylundecanal (aldehyde C12 MNA), aldehyde C-14 (gamma-undecalactone; 1,4-undecanolide), cyclamen aldehyde (2-methyl-3-(4-isobutylphenyl)-propanal), ambrocenide ((4aR,5R,7aS,9R)-octahydro- 2,2,5,8,8,9a-hexamethyl-4h-4a,9-methanoazuleno(5,6-d)-1,3-dioxole), benzyl acetate, betaionone, isoamyl butyrate, calone (calone 1951, watermelon ketone, 7- methylbenzo[b][1 ,4]dioxepin-3-one), cetalox (naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a- tetramethyl-), cis-3-hexenyl isobutyrate, corps cassis, dartanol (also known as bacdanol, sandolene, topanzol or 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), dupical (4-(octahydro-4,7-methano-5H-inden-5-ylidene)butanal), ethyl maltol (2 ethyl-3-hydroxy-4H- pyran-4-one), ethyl vanillin (4-hydroxy-3-ethoxybenzaldehyde), floralozone (florone, florazon, 3-(4-ethylphenyl)-2,2-dimethylpropanal), galbascone (dynascone; 1-(5,5-dimethyl-1 cyclo_'hexen-1-yl)-4-penten-1-one), gamma-decalactone (1,4-decanolide), gamma-

[0243] M / BASFTR-2475-PC 230961W001

[0244] 31 octalactone (4-octanolide), geranyl acetate, habanolide (trans- 11-pentadecen- 1,15-olide; cis and trans- 12-pentadecen-1, 15-olide), allyl heptanoate, hexyl acetate, indol, Iso E Super, isobutyl quinoleine, isoeugenol, javanol, lemonile, limette distillee, manzanate (ethyl 2- methylpentanoate), delta-muscenone, oxane, peonile, prenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl salicylate, isoamyl salicylate, stemone, tetrahdrolinalool, triplal (ligustral; vertocitral; trivertal; 2,4-dimethyl-3-cyclohexenecarbox-aldehyde), undecavertol (4-methyl-3- decen-5-ol), verdox (OTBCH, 2-tert-butylcyclohexyl acetate), violettyne (1,3-undecadien-5- yne), allyl 3-cyclohexylpropionate, allyl heptylate, ambroxide (ambrox; ambroxan; 3a, 6, 6, 9a tetramethyldodecahydronaphtho_'[2,1-b]furan), bacdanol (topanzol; sandolen; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), citronellyl acetate, cyclopentadecanolide (15-pentadecanolacton), damascenone, dihydromyrcenol, dimethyl benzyl carbinyl butyrate (alpha, alpha-dimethylphenylethyl butyrate), ethyl butyrate, ethyl maltol, ethyl 2- m ethyl butyrate, evernyl (methyl 2,4-dihydroxy-3,6-dimethylbenzoate), fructalate, hedione, hexyl isobutyrate, isoamyl acetate, methyl benzoate, methyl propyl oxathiane, para-cresyl methyl ether, phenoxyethyl isobutyrate, phenylethyl alcohol, pyranol (florol; 2-isobutyl-4- methyltetrahydro-2H pyran-4-ol), verdyl propionate (3a,4,5,6,7,7a-hexahydro-4,7-methano- 1 H-inden-5(6)-yl propionate), 8-mercapto-menthanone, aldehyde C-18 (gammanonalactone; 5-pentyloxolan-2-one), alpha-ionone, citronellyl nitrile, cyclabute (tricyclodecenyl isobutyrate; 3a,4,5,6,7,7a-hexahydro-4,7-methano-1 H-inden-5(6)-yl isobutyrate), alpha-damascone, helvetolide, hexyl salicylate, hydratropic aldehyde dimethyl acetal (2-phenylpropionaldehyde dimethyl acetal), limonene, linalyl acetate, melonal, orange oil, para-menthenethiol, styrallyl acetate (1 -phenylethyl acetate), terpenyl acetate, hydroxycitronellal, amylvinylcarbinol (1-octen-3-ol), camphor, ethyl linalool, eucalyptol (cineol), hexyl butyrate, hexyl caproate (hexyl hexanoate), isoborneol, linalool oxide (2-(5- methyl-5-vinyltetrahydro-1-furyl)-2-propanol), methyl hexyl ketone (2-octanone), methyl octalactone (whisky lactone, 3-methyl-4-octanolide, 3-methyl-1, 4-octanolide, 5-butyl-4- methyloxolan-2-one), ocimene, octyl acetate, terpineol alpha, terpinolene, terpinly acetate, para-cymene (1-methyl-4-(propan-2-yl)benzene, 4-isopropyltoluene) and mixtures thereof.

[0245] Non-aroma chemical carrier:

[0246] The non-aroma chemical carrier in the composition of the invention is preferably selected from the group consisting of surfactants, oil components antioxidants, deodorant-active agents and solvents.

[0247] Preferably the at least one non-aroma chemical carrier is a compound, a mixture of compounds or other additives, which has / have no or no noteworthy sensory properties. The non-aroma chemical carrier can serve for the dilution and / or the fixing of the compounds of formula (I) and optionally compound (II) and / or the at least one aroma chemical (X), as defined above, if comprised in the composition.

[0248] M / BASFTR-2475-PC 230961W001

[0249] 32

[0250] The non-aroma chemical carrier in the composition of the invention is preferably selected from the group consisting of surfactants, oil components, solvents or any mixture of two or more of the aforementioned.

[0251] Solvent

[0252] In the context of the present invention, a "solvent" serves for the dilution of the compounds of formula (I) (and (II), if applicable) to be used according to the invention without having its own aroma.

[0253] The amount of solvent(s) is selected depending on the composition.

[0254] Preferably, the solvent is present in the composition in a total amount of 0.01 wt.% to 99.0 wt.%, more preferably in a total amount of 0.05 wt.% to 95.0 wt.%, yet more preferably in a total amount of 0.1 wt.% to 80.0 wt.%, most preferably 0.1 wt.% to 70.0 wt.%, particularly in a total amount of 0.1 wt.% to 60.0 wt.%, based on the total weight of the composition.

[0255] In a preferred embodiment, the composition comprises 0.05 wt.% to 10 wt.%, more preferably 0.1 wt.% to 5 wt.%, yet more preferably 0.2 wt.% to 3 wt.% total solvent(s), based on the total weight of the composition. In yet another preferred embodiment of the invention, the composition comprises 20 wt.% to 70 wt.%, more preferably 25 wt.% to 50 wt.% of total solvent(s), based on the total weight of the composition.

[0256] Preferred solvents are selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, triethyl citrate, isopropyl myristate, diethyl phthalate, benzyl benzoate and any mixture of two or more of the aforementioned.

[0257] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and at least one solvent and optionally at least one aroma chemical (X).

[0258] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one solvent.

[0259] In another preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one solvent and optionally at least one aroma chemical (X).

[0260] M / BASFTR-2475-PC 230961W001

[0261] 33

[0262] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one solvent.

[0263] Oil component

[0264] Preferably, the total oil components are present in an amount of 0.1 to 80 wt.%, more preferably 0.5 to 70 wt.%, yet more preferably 1 to 60 wt.%, even more preferably 1 to 50 wt.%, particularly 1 to 40 wt.%, more particularly 5 to 25 wt.% and specifically 5 to 15 wt.%, based on the total weight of the composition.

[0265] Preferably the oil components are selected from Guerbet alcohols based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms and other additional esters, such as 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, isostearyl 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. Also suitable are esters of C18-C38 alkylhydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, more especially dioctyl malate, esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer dial or trimer triol), triglycerides based on C6-C10 fatty acids, liquid mono-, di- and triglyceride mixtures based on C6-C18 fatty acids, esters of C6- C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 car- bon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates such as, for example, dicaprylyl carbonate (Cetiol® CO), Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, esters of benzoic acid with linear and / or branched C6 to C22 alcohols (for example Finsolv® TN), linear or branched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group such as, for example, dicaprylyl ether (Cetiol® OE), ring opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof.

[0266] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one oil component and optionally at least one aroma chemical (X).

[0267] M / BASFTR-2475-PC 230961W001

[0268] 34

[0269] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one oil component.

[0270] In another preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one oil component and optionally at least one aroma chemical (X).

[0271] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one oil component.

[0272] Antioxidants

[0273] It is to be understood that antioxidants are able to inhibit or prevent the undesired changes in the compositions to be protected caused by oxygen effects and other oxidative processes. The effect of the antioxidants consists in most cases in them acting as free-radical scavengers for the free radicals which arise during autoxidation.

[0274] In a preferred embodiment, the antioxidant is selected from the group consisting of

[0275] • amino acids (for example glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and derivatives thereof,

[0276] • imidazoles (e.g. urocanic acid) and derivatives thereof,

[0277] • peptides, such as D,L-carnosine, D-carnosine, L-carnosine (=|3-Alanyl-L-histidine) and derivatives thereof,

[0278] • carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene, lutein) or derivatives thereof,

[0279] • chlorogenic acid and derivatives thereof,

[0280] • lipoic acid and derivatives thereof (for example dihydrolipoic acid),

[0281] • auro-thioglucose, propylthiouracil and other thiols (for example thioredoxin, glutathione, cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters thereof) and salts thereof,

[0282] • dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

[0283] • sulfoximine compounds (for example buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptathionine sulfoximine),

[0284] • (metal) chelating agents (e.g. alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

[0285] M / BASFTR-2475-PC 230961W001

[0286] 35

[0287] • alpha-hydroxy acids (for example citric acid, lactic acid, malic acid),

[0288] • humic acid, bile acid, bile extracts, bilirubin, biliverdin, boldin (= alkaloid from the plant Peumus boldus, boldo extract,

[0289] • EDTA, EGTA and derivatives thereof,

[0290] • unsaturated fatty acids and derivatives thereof (e.g. gamma-linolenic acid, linoleic acid, oleic acid),

[0291] • folic acid and derivatives thereof,

[0292] • ubiquinone and ubiquinol and derivatives thereof,

[0293] • vitamin C and derivatives (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate),

[0294] • tocopherols and derivatives (for example vitamin E acetate),

[0295] • vitamin A and derivatives (for example vitamin A palmitate),

[0296] • coniferyl benzoate of gum benzoin, rutic acid and derivatives thereof, alpha- glycosylrutin, ferulic acid, furfurylideneglucitol,

[0297] • butylhydroxytoluene (BHT), butylhydroxyanisole (BHA)

[0298] • nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof,

[0299] • superoxide dismutase,

[0300] • zinc and derivatives thereof (for example ZnO, ZnSO4),

[0301] • selenium and derivatives thereof (for example selenomethionine),

[0302] • stilbenes and derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and mixtures of two or more of the aforementioned.

[0303] In a preferred embodiment, the anti-oxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate, tocopherol and mixtures of two or more of the aforementioned.

[0304] Preferably, the compositions according to the present invention comprise the anti-oxidant in a total amount of 0.001 to 25 wt.-%, preferably 0.005 to 10 wt.-%, more preferably 0.01 to 8 wt.-%, yet more preferably 0.025 to 7 wt.-%, even more preferably 0.05 to 5 wt.-%, based on the total weight of the composition.

[0305] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one antioxidant and optionally at least one aroma chemical (X).

[0306] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least antioxidant.

[0307] M / BASFTR-2475-PC 230961W001

[0308] 36

[0309] In another preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one antioxidant and optionally at least one aroma chemical (X).

[0310] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one antioxidant.

[0311] Deodorant-active aqents

[0312] Deodorizing compositions (deodorants and antiperspirants) counteract, mask or eliminate body odors. Body odors are formed through the action of skin bacteria on apocrine perspiration which results in the formation of unpleasant-smelling degradation products.

[0313] Preferably the deodorant-active agent is selected from the groups consisting of antiperspirants, esterase inhibitors, antibacterial agents and mixtures of two or more of the aforementioned.

[0314] Suitable antiperspirants are selected from the group consisting of salts of aluminum, zirconium or zinc. Examples are aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and complex compounds thereof, for example with 1 ,2-propylene glycol, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and complex compounds thereof, for example with amino acids, such as glycine. Aluminum ch loro hydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and complex compounds thereof are preferably used.

[0315] Preferably, the anti-perspirant is selected from the group consisting of aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium tri ch loro hydrate, aluminum zirconium tetrachlorohydrate aluminum zirconium pentachlorohydrate and mixtures of two or more of the aforementioned.

[0316] Where perspiration is present in the underarm region, extracellular enzymes-esterases, mainly proteases and / or lipases are formed by bacteria and split the esters present in the perspiration, releasing odors in the process. Suitable esterase inhibitors are for example trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate. Esterase inhibitors inhibit enzyme activity and thus reduce odor formation. The free acid is probably released by the cleavage of the citric acid ester and

[0317] M / BASFTR-2475-PC 230961W001

[0318] 37 reduces the pH value of the skin to such an extent that the enzymes are inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, 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 esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, zinc glycinate and mixtures of two or more of the aforementioned.

[0319] Preferably, the esterase inhibitor is 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 glycinate and mixtures of two or more of the aforementioned.

[0320] Preferably, the compositions according to the present invention comprise the esterase inhibitor in a total amount in the range of 0.01 to 20 wt.-%, preferably 0.1 to 10 wt.-% and more particularly 0.5 to 5 wt.-%, based on the total weight of the composition.

[0321] The term “anti-bacterial agents” as used herein encompasses substances which have bactericidal and / or bacteriostatic properties. Typically these substances act against grampositive bacteria such as, for example, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (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-propinyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides such as, for example, salicylic acid-n-octyl amide or salicylic acid-n-decyl amide.

[0322] Preferably, the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'- hydroxydiphenylether (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-propinyl butyl carbamate, chlorhexidine, 3,4,4'- trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides and mixtures of two or more of the aforementioned.

[0323] M / BASFTR-2475-PC 230961W001

[0324] 38

[0325] Preferably, the composition according to the present invention comprises the antibacterial agent(s) in a total amount in the range of 0.01 to 5 wt.% and preferably 0.1 to 2 wt.-%, based on the total weight of the composition.

[0326] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one deodorant active agent and optionally at least one aroma chemical (X).

[0327] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one deodorant active agent.

[0328] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one deodorant active agent and optionally at least one aroma chemical (X).

[0329] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one deodorant active agent.

[0330] Surfactants

[0331] Preferably, the surfactant is selected from the group consisting of anionic, non-ionic, cationic, amphoteric, zwitterionic surfactant and a mixture of two or more of the aforementioned. More preferably, the surfactant is an anionic surfactant.

[0332] Preferably, the compositions according to the invention contain the surfactant(s), in a total amount of 0 to 40 wt.%, more preferably 0 to 20 wt.%, more preferably 0.1 to 15 wt.%, and particularly 0.1 to 10 wt.%, based on the total weight of the composition.

[0333] Preferable nonionic 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 partly oxidized alk(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolysates (particularly wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the non-ionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, although they preferably have a narrow-range homolog distribution.

[0334] M / BASFTR-2475-PC 230961W001

[0335] 39

[0336] Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one COO(-) or SOa(-) group in the molecule.

[0337] Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl- N,N-dimethyl ammonium glycinates, for example, cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example, cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. The fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred.

[0338] Ampholytic surfactants are also suitable, particularly as co-surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C-8 to C-18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and which are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N- alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N- alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N- cocoalk-yl amino propionate, cocoacyl amino ethyl amino propionate and acyl sarcosine.

[0339] Anionic surfactants are characterized by a water-solubilizing anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic group. Dermatologically safe anionic surfactants are known to the practitioner in large numbers from relevant textbooks and are commercially available. They are, in particular, alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts, alkylether sulfates, alkylether carboxylates, acyl isethionates, acyl sarcosinates, acyl taurines containing linear C-12-C-18 alkyl or acyl groups and sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.

[0340] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more especially chlorides and bromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl ammonium chlorides and trialkyl methyl ammonium chlorides, for example, cetyl trimethyl ammonium chloride, stearyl trim ethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride. In addition, the readily biodegradable quaternary ester compounds, such as, for example, the dialkyl ammonium methosulfates and methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the name of Stepantexe and the corresponding products of the Dehyquart® series, may be used as cationic surfactants. “Esterquats” are generally understood to be quaternized fatty acid triethanolamine ester salts. They can provide the compositions with particular softness. They are known substances which are prepared by

[0341] M / BASFTR-2475-PC 230961W001

[0342] 40 the relevant methods of organic chemistry. Other cationic surfactants suitable for use in accordance with the invention are the quaternized protein hydrolysates.

[0343] Due to the characteristic sensory property of the compound of formula (I) [or of its mixture with compounds (II)] and its substantivity, tenacity as well as stability, it can especially be used to provide an odor, preferably a fragrance impression to surfactant-containing compositions such as, for example, cleaners (such as laundry care products and all-purpose cleaners).

[0344] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one surfactant and optionally at least one aroma chemical (X).

[0345] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one surfactant.

[0346] In a preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one surfactant and optionally at least one aroma chemical (X).

[0347] In an alternatively preferred embodiment, the composition comprises the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, and at least one aroma chemical (X) and optionally at least one surfactant.

[0348] Suitable compositions are for example perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0349] Perfume compositions can be selected from fine fragrances, air fresheners in liquid form, gel-like form or a form applied to a solid carrier, aerosol sprays, scented cleaners, perfume candles and oils, such as lamp oils or oils for massage.

[0350] Examples for fine fragrances are perfume extracts, Eau de Parfums, Eau de Toilettes, Eau de Colognes, Eau de Solide and Extrait Parfum.

[0351] Body care compositions include cosmetic compositions and products for oral and dental hygiene, and can be selected from after-shaves, pre-shave products, splash colognes, solid

[0352] M / BASFTR-2475-PC 230961W001

[0353] 41 and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water type, of the water-in-oil type and of the water-in-oil-in-water type, such as e.g. skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products such as e.g. hairsprays, hair gels, setting hair lotions, hair conditioners, hair shampoo, permanent and semi-permanent hair colorants, hair shaping compositions such as cold waves and hair smoothing compositions, hair tonics, hair creams and hair lotions, deodorants and antiperspirants such as e.g. underarm sprays, roll-ons, deodorant sticks and deodorant creams, products of decorative cosmetics such as e.g. eye-liners, eyeshadows, nail varnishes, make-ups, lipsticks and mascara, and products for oral and dental hygiene, such as toothpaste, dental floss, mouth wash, breath fresheners, dental foam, dental gels and dental strips.

[0354] Hygiene articles can be selected from joss sticks, insecticides, repellents, propellants, rust removers, perfumed freshening wipes, armpit pads, baby diapers, sanitary towels, toilet paper, cosmetic wipes, pocket tissues, dishwasher and deodorizer.

[0355] Cleaning compositions, such as e.g. cleaners for solid surfaces, can be selected from perfumed acidic, alkaline and neutral cleaners, such as e.g. floor cleaners, window cleaners, dishwashing compositions both for handwashing and machine washing use, bath and sanitary cleaners, scouring milk, 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, mold removers, facade cleaners.

[0356] Textile detergent compositions can be selected from liquid detergents, powder detergents, laundry pre-treatments such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets.

[0357] Food means a raw, cooked, or processed edible substance, ice, beverage or ingredient used or intended for use in whole or in part for human consumption, or chewing gum, gummies, jellies, and confectionaries.

[0358] A food supplement is a product intended for ingestion that contains a dietary ingredient intended to add further nutritional value to the diet. A dietary ingredient may be one, or any combination, of the following substances: a vitamin, a mineral, an herb or other botanical, an amino acid, a dietary substance for use by people to supplement the diet by increasing the total dietary intake, a concentrate, metabolite, constituent, or extract. Food supplements may be found in many forms such as tablets, capsules, soft gels, gel caps, liquids, or powders.

[0359] M / BASFTR-2475-PC 230961W001

[0360] 42

[0361] Pharmaceutical compositions comprise compositions which are 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 body of man or other animals.

[0362] Crop protection compositions comprise compositions which are intended for the managing of plant diseases, weeds and other pests (both vertebrate and invertebrate) that damage agricultural crops and forestry.

[0363] Preferably, the compositions according to the invention further comprises at least one auxiliary agent selected from the group consisting of preservatives, abrasives, anti-acne agents, agents to combat skin aging, anti-cellulite agents, antidandruff agents, antiinflammatory agents, irritation-preventing agents, irritation-alleviating agents, astringents, sweat-inhibiting agents, antiseptics, anti-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, care agents, hair removal agents, emulsifiers, enzymes, essential oils, fibres, film formers, fixatives, foam formers, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair smoothing agents, moisture-donating agents, moisturizing substances, humectant substances, bleaching agents, strengthening agents, stain removal agents, optical brighteners, impregnating agents, soil repellents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifiers, plasticizers, covering agents, polish, shine agents, polymers, powders, proteins, refatting agents, exfoliating agents, silicones, skincalming agents, skin-cleansing agents, skin care agents, skin-healing agents, skin lightening agents, skin-protective agents, skin-softening agents, cooling agents, skin-cooling agents, warming agents, skin-warming agents, stabilizers, UV-absorbent agents, UV filters, fabric softeners, suspending agents, skin-tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono or polyunsaturated fatty acids, alpha hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color-protection agents, pigments, anticorrosives, polyols, electrolytes and silicone derivatives.

[0364] Preparation of compositions and methods to impart an aroma impression to a composition

[0365] One embodiment of the present invention is directed to a method for preparing a composition of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or of a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, where the composition further comprises:

[0366] (i) at least one aroma chemical (X) other than compounds according to the present invention or

[0367] (ii) at least one non-aroma chemical carrier, or

[0368] (iii) both of (i) and (ii).

[0369] M / BASFTR-2475-PC 230961W001

[0370] 43

[0371] For example, the method can be carried out by mixing the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture comprising the compound (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof and:

[0372] (i) at least one aroma chemical (X), or

[0373] (ii) at least one non-aroma chemical carrier, or

[0374] (iii) both of (i) and (ii).

[0375] The invention is also directed to a method for boosting the aroma impression of a composition, wherein the method comprises incorporating the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof into a composition, or mixing simultaneously or sequentially the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof with a part or with all other components of the desired composition.

[0376] In particular, the invention is directed to a method of preparing a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, comprising including at least one compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof in a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition; or mixing simultaneously or sequentially the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof with a part or with all other components of said compositions.

[0377] In one embodiment the invention is directed to a method for imparting a floral violet, fruity, marine, or technical metallic note or any combination of such notes to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof in a

[0378] M / BASFTR-2475-PC 230961W001

[0379] 44 perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, or mixing simultaneously or sequentially the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof with a part or with all other components of said compositions. In this case, the compound (I) is specifically present as the pure Z isomer or a mixture of the Z and E isomers containing at least 90%by weight of the Z isomer, relative to the total amount of the Z and E isomers.

[0380] In another embodiment the invention is directed to a method for imparting a fresh, natural, citrus (mandarine) or sparkling note with a metallic connotation or any combination of such notes to a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including a mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof in a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, or mixing simultaneously or sequentially the mixture of the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof and the compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof with a part or with all other components of said compositions. In this case, the compound (I) is specifically present as the pure Z isomer or a mixture of the Z and E isomers containing at least 90% by weight of the Z isomer, relative to the total amount of the Z and E isomers, and the mixture comprises 0.15 to 1.5% by weight of the compound (I), relative to the total amount of compounds (I) and (II).

[0381] Amounts

[0382] Generally, the total amount of compounds of formula (I) in the compositions, methods and uses according to the present invention is typically adapted to the particular intended use or the intended application and can, thus, vary over a wide range. As a rule, the customary standard commercial amounts for aroma chemicals, preferably for scents are used. Preferably the compositions according to the invention comprise the compound of formula (I) in a total amount of 0.001 to 99.9 wt.%, based on the total weight of the composition. Particularly, the compositions comprise the compound of formula (I) in a total amount of 0.001 to 99.5 wt.%, preferably of 50 to 99 wt.%, more preferably of 80 to 95 wt.% and in particular of 90 to 95 wt.%, based on the total weight of the composition.

[0383] Particularly, the compositions comprise the compound of formula (I) in a total amount of 0.005 to 80 wt.%, preferably of 0.01 to 30 wt.%, more preferably of 1 to 20 wt.%, and in particular of 5 to 15 wt.%, based on the total weight of the composition.

[0384] M / BASFTR-2475-PC 230961W001

[0385] 45

[0386] Particularly, the compositions comprise the compound of formula (I) in a total amount of 0.001 to 20 wt.%, preferably of 0.01 to 10 wt.%, more preferably of 0.01 to 6 wt.% or 0.005 to 6 wt.%, even more preferably of 0.01 to 5 wt.% or 0.01 to 4 wt.%, and in particular of 0.01 to 3 wt.%, based on the total weight of the composition.

[0387] Preferably the compositions according to the invention comprise the mixture of the compounds of formula (I) and formula (II) in a total amount of 0.001 to 99.9 wt.%, based on the total weight of the composition.

[0388] Particularly, the compositions comprise the mixture of the compounds of formula (I) and formula (II) in a total amount of 0.001 to 99.5 wt.%, preferably of 50 to 99 wt.%, more preferably of 80 to 95 wt.% and in particular of 90 to 95 wt.%, based on the total weight of the composition.

[0389] Particularly, the compositions comprise the mixture of the compounds of formula (I) and formula (II) in a total in a total amount of 0.005 to 80 wt.%, preferably of 0.01 to 30 wt.%, more preferably of 1 to 20 wt.%, and in particular of 5 to 15 wt.%, based on the total weight of the composition.

[0390] Particularly, the compositions comprise the mixture of the compounds of formula (I) and formula (II) in a total amount of 0.001 to 20 wt.%, preferably of 0.01 to 10 wt.%, more preferably of 0.01 to 6 wt.% or 0.005 to 6 wt.%, even more preferably of 0.01 to 5 wt.% or 0.01 to 4 wt.%, and in particular of 0.01 to 3 wt.%, based on the total weight of the composition.

[0391] EXAMPLES

[0392] The present invention is illustrated in detail by non-restrictive working examples which follow. More particularly, the test methods specified hereinafter are part of the general disclosure of the application and are not restricted to the specific working examples.

[0393] 1 . Analytical method:

[0394] The characterization is done by13C NMR and1H NMR. The13C NMR and1H NMR spectra were measured on a Bruker DPX-500 spectrometer.

[0395] GC method as applied in the synthesis of compound (I): column: ZebronZB-5, 30 m, ID: 0.25 mm, film: 1.0 pm; oven: 40-5-10 / 280-21 ; injection volume: 0.20 pL

[0396] GC method as applied in the synthesis of compound (II): column: DB-5, 30 m, ID: 0.32 mm, film: 1.0 pm; oven: 40°C-0min-20oC / min-115oC-18min-20oC / min-280°C-5min lnj. / Det.250°C / 320°C; gas: 0.8 mL / min N2, injection volume: 0.20 pL cis-4-Heptenal and 2-octanol were used as the commercial products (available, for example, from Sigma Aldrich).

[0397] M / BASFTR-2475-PC 230961W001

[0398] 46

[0399] 2. Synthesis of compound (I)

[0400] Step 1

[0401] Methylmagnesium bromide (CHsMgBr) (3.0 M in diethylether (Et20), 18.1 g, 52.37 mmol) was added dropwise to a stirred solution of cis-4-heptenal (4.2 g, 36.69 mmol) in anhydrous tetrahydrofuran (THF) (250 mL) at 0°C. The resulting mixture was stirred at 0°C for 30 min. The reaction was terminated by addition of a saturated aqueous NH4CI solution, the layers were separated, the aqueous layer was extracted with methyl-tert-butyl ether (MTBE) (3x), the combined organic layers were washed with brine, dried over MgSC>4, filtered and concentrated in vacuo to obtain a colorless oil. The crude product was directly used for the next step. (GC-tR = 12.938 min)

[0402] Step 2

[0403] The crude alcohol obtained in step 1 was dissolved in acetic anhydride (7.3 g, 71.51 mmol) and acetic acid (0.3 g, 5.00 mmol) and Nation NR50 (0.40 g) (acidic ion exchange resin) was added. The resulting mixture was stirred until completion was observed by GC analysis. The reaction was terminated by addition of water. The ion exchange resin was removed by filtration and the aqueous layer was extracted with MTBE (3x), the organic layers were neutralized with a saturated aqueous NaHCOs-solution and washed with brine. The aqueous layer was dried over MgSO4, filtered and concentrated in vacuo. Vacuum distillation (25.6- 26.3°C, 0.15 mbar) yielded the acetate as a colorless oil [5.7 g, 33.54 mmol, 92% as 95:5 - mixture of cis:trans (Z:E)]. (GC-tR = 15.268 min)

[0404] 1H NMR (500 MHz, CDCI3): 5 = 5.37 (m, 1 H), 5.30 (m, 1 H), 4.90 (m, 1 H), 2.07 (m, 2H), 2.03 (s, 3H), 2.01 (m, 2H), 1.63 (m, 2H), 1.21 (d, 3H), 0.95 (t, 3H) ppm.

[0405] 13C NMR (125 MHz, CDCI3): 5 = 170.8, 132.4, 127.9, 70.6, 28.6 (trans), 25.6 (trans), 23.1 , 21.4, 20.5, 20.0, 14.3 ppm.

[0406] 3. Synthesis of compound (II)

[0407] 2-Octanol (25 g, 191 ,9 mmol) was dissolved in acetic anhydride (28.8 g, 282.1 mmol) and acetic acid (1.1 g, 18.8 mmol) and Nation NR50 (acidic ion exchange resin) (0.50 g) was added. The resulting mixture was stirred until completion was observed by GC analysis. The reaction was terminated by addition of water. The ion exchange resin was removed by filtration and the aqueous layer was extracted with MTBE (3x), the organic layers were neutralized with a saturated aqueous NaHCOs-solution and washed with brine. The aqueous layer was dried over MgSO4, filtered and concentrated in vacuo to yield the acetate as a colorless oil (28.6 g, 165.2 mmol, 86%). (GC-tR= 21.55 min)

[0408] 1H NMR (500 MHz, CDCI3): 5 = 4.9-4.8 (m, 1 H), 2.0 (s, 3H), 1.75-1.4 (m, 2H), 1.4-1.0 (m, 11 H), 1.0-0.7 (m, 3H) ppm.

[0409] M / BASFTR-2475-PC 230961W001

[0410] 47

[0411] 13C NMR (125 MHz, CDCI3): 5 = 170.8, 71.1, 36.0, 31.8, 29.2, 25.4, 22.6, 21.4, 20.0, 14.1 ppm.

[0412] Mixtures of compounds (I) and (II) were prepared by mixing the products of examples 2 and 3 in the desired ratios.

[0413] 4. Olfactory impression

[0414] In order to test the quality and intensity of the compounds of the present invention and the mixtures, scent strip tests were performed; also the pure form was tested.

[0415] For this purpose, the compound (mixture) was olfactively evaluated by a panel of trained experts both in pure form and in dilution. For testing in diluted form, strips of absorbent paper were dipped into a solution containing 1 to 10 wt.% of the compound (mixture) to be tested in triethyl citrate. After evaporation of the solvent (about 30 s) the scent impression was olfactively evaluated by a panel of trained experts.

[0416] Aroma impression of the compounds (I) and (II) and various mixtures thereof are indicated in the below table 1. The aroma descriptors of the pure form and the diluted form are identical. The compounds and the mixtures were formulated in the perfume compositions according to tables 2 to 7 and were labelled as compound 1 in Tables 2 to 5 and as compound A in Tables 6 and 7.

[0417] Table 1 : Compounds and mixtures of the present invention

[0418] M / BASFTR-2475-PC 230961W001

[0419] 48

[0420] 5. Advantageous compositions I

[0421] 5.1 Perfume composition suitable for liquid laundry detergent composition and ready-to-use liquid detergent composition containing this perfume composition

[0422] A perfume composition which is suitable for use in a liquid laundry detergent composition was prepared by mixing the fragrances listed in table 2 in the indicated amounts. Table 2

[0423] M / BASFTR-2475-PC 230961W001

[0424] 49

[0425] Compound 1 is either compound I or compound II or a mixture of compounds I and II in a weight ratio of 0.25:99.75. The respective resulting fragrance impressions are described in the following.

[0426] M / BASFTR-2475-PC 230961W001

[0427] 50

[0428] Perfume compositions A and B were tested as 10 wt.% solutions in triethyl citrate. Strips of absorbent paper were dipped into these solutions. The scent impression was olfactively evaluated by a panel of trained experts.

[0429] Additionally, perfume compositions A and B were worked into a commercial non-scented liquid laundry detergent base for sensitive skin (concentration of perfume compositions A and B in the liquid laundry detergent base: 0.7% by weight). The scent impression was olfactively evaluated by a panel of trained experts.

[0430] The liquid laundry detergent base contained following ingredients:

[0431] - 5-15% non-ionic and anionic surfactants, soap

[0432] - <5% phosphonates

[0433] - optical brightener

[0434] - water

[0435] The panel of trained experts judged for the triethyl citrate solutions as well as for the liquid laundry detergents as follows:

[0436] Perfume composition A I liquid laundry detergent containing composition A has a blooming, floral, fruity musk fragrance.

[0437] Perfume composition B I liquid laundry detergent containing composition B containing compound I as compound A, respectively:

[0438] Compared to perfume composition A I liquid laundry detergent containing composition A, the floral aspects are more pronounced.

[0439] Perfume composition B I liquid laundry detergent containing composition B containing compound II as compound 1:

[0440] Compared to perfume composition A I liquid laundry detergent containing composition A, the accord becomes more aldehydic and fresh.

[0441] Perfume composition B I liquid laundry detergent containing composition B containing compounds I and II in a weight ratio of 0.25:99.75 as compound 1 :

[0442] Compared to perfume composition A I liquid laundry detergent containing composition A, the aldehydic push observed in perfume composition B I liquid laundry detergent containing composition B containing compound II as compound 1 is combined with floral violet aspects.

[0443] 5.2 Perfume composition suitable for shampoos and ready-to-use shampoos containing this perfume composition

[0444] A perfume composition which is suitable for use in a shampoo was prepared by mixing the fragrances listed in table 3 in the indicated amounts.

[0445] M / BASFTR-2475-PC 230961W001

[0446] 51

[0447] Table 3

[0448] M / BASFTR-2475-PC 230961W001

[0449] 52

[0450] * Compound 1 is either compound I or compound II or a mixture of compounds I and II in a weight ratio of 0.25:99.75. The respective resulting fragrance impressions are described in the following.

[0451] Perfume compositions A and B were tested as 10 wt.% solutions in triethyl citrate. Strips of absorbent paper were dipped into these solutions. The scent impression was olfactively evaluated by a panel of trained experts.

[0452] Additionally, perfume compositions A and B were worked into a commercial non-scented shampoo base (concentration of perfume compositions A and B in the shampoo: 1% by weight). The scent impression was olfactively evaluated by a panel of trained experts.

[0453] The shampoo base contained following ingredients:

[0454] - Water

[0455] - Sodium laureth sulfate

[0456] - Sodium chloride

[0457] - Cocoamidopropyl betaine

[0458] - Behanoyl PG-trimonium chloride

[0459] - Disodium cocoyl glutamate

[0460] - Hexylene glycol

[0461] - Citric acid

[0462] - Sodium benzoate

[0463] - Sorbic acid

[0464] The panel of trained experts judged for the triethyl citrate solutions as well as for the shampoos as follows:

[0465] Perfume composition A I shampoo containing composition A has a fruity fragrance with apple notes and a citrus impression.

[0466] Perfume composition B I shampoo containing composition B containing compound I as compound A, respectively:

[0467] M / BASFTR-2475-PC 230961W001

[0468] 53

[0469] Compared to perfume composition A I shampoo containing composition A, the fragrance becomes more fruity and sweet, but less fresh.

[0470] Perfume composition B I shampoo containing composition B containing compound II as compound A, respectively:

[0471] Compared to perfume composition A I shampoo containing composition A, the fragrance is nearly unchanged.

[0472] Perfume composition B I shampoo containing composition B containing compounds I and II in a weight ratio of 0.25:99.75 as compound 1 :

[0473] Compared to perfume composition A I shampoo containing composition A, there is a very nice effect; the fragrance becomes juicier and fresher.

[0474] 5.3 Perfume composition suitable for liquid dishwashing detergent composition and ready-to- use liquid dishwashing detergent composition containing this perfume composition

[0475] A perfume composition which is suitable for use in a liquid dishwashing detergent composition was prepared by mixing the fragrances listed in table 4 in the indicated amounts. The composition is also suitable for an all-purpose cleaner.

[0476] Table 4

[0477] M / BASFTR-2475-PC 230961W001

[0478] 54

[0479] Compound 1 is either compound I or compound II or a mixture of compounds I and II in a weight ratio of 0.25:99.75. The respective resulting fragrance impressions are described in the following.

[0480] Perfume compositions A and B were tested as 10 wt.% solutions in triethyl citrate. Strips of absorbent paper were dipped into these solutions. The scent impression was olfactively evaluated by a panel of trained experts.

[0481] Additionally, perfume compositions A and B were worked into a commercial non-scented liquid dishwashing detergent base for sensitive skin (concentration of perfume compositions A and B in the liquid dishwashing detergent base: 0.7% by weight). The scent impression was olfactively evaluated by a panel of trained experts.

[0482] The liquid dishwashing detergent base contained following ingredients:

[0483] - Water

[0484] - Sodium laureth sulfate

[0485] - Cocoamidopropyl betaine

[0486] - C10 Pareth-8

[0487] - Citric acid

[0488] - Sodium xylene sulfonate

[0489] - Sodium benzoate

[0490] M / BASFTR-2475-PC 230961W001

[0491] 55

[0492] - Sodium chloride

[0493] The panel of trained experts judged for the triethyl citrate solutions as well as for the liquid dishwashing detergents as follows:

[0494] Perfume composition A I liquid dishwashing detergent containing composition A has an exotic fragrance with citric aspects.

[0495] Perfume composition B I liquid dishwashing detergent containing composition B containing compound I as compound A, respectively:

[0496] Compared to perfume composition A I liquid dishwashing detergent containing composition A, sweet aspects are added.

[0497] Perfume composition B I liquid dishwashing detergent containing composition B containing compound II as compound 1:

[0498] Compared to perfume composition A I liquid dishwashing detergent containing composition A, the accord becomes fresher and juicier with some orange notes.

[0499] Perfume composition B I liquid dishwashing detergent containing composition B containing compounds I and II in a weight ratio of 0.25:99.75 as compound 1 :

[0500] Compared to perfume composition A I liquid dishwashing detergent containing composition A, the fruitiness is clearly enhanced, and on top, white floral aspects are added. The addition of this mixture really rounds up the composition.

[0501] 5.4 Perfume composition suitable for personal care compositions, such as body creams

[0502] A perfume composition which is suitable for use in a personal care composition, especially a body cream, was prepared by mixing the fragrances listed in table 5 in the indicated amounts.

[0503] Table 5

[0504] M / BASFTR-2475-PC 230961W001

[0505] 56

[0506] Compound 1 is a mixture of compounds I and II in a weight ratio of 0.25:99.75. The respective resulting fragrance impressions are described in the following. Perfume compositions A and B were tested as 10 wt.% solutions in triethyl citrate. Strips of absorbent paper were dipped into these solutions. The scent impression was olfactively evaluated by a panel of trained experts. These judged as follows:

[0507] Perfume composition A features a low-allergen lavender scent designed for personal care applications, such as body creams.

[0508] Perfume composition B:

[0509] Compared to perfume composition A, the fragrance profile becomes more natural and floral.

[0510] The addition of compound 1 also introduces a coumarinic (sweet) note, enhancing the overall olfactory experience.

[0511] Moreover, compared to perfume composition A, perfume composition B demonstrates an improved tenacity on the test strip, offering a longer-lasting scent impression.

[0512] M / BASFTR-2475-PC 230961W001

[0513] 57

[0514] 6. Advantageous compositions II

[0515] The compounds and the mixtures as indicated in table 1 were formulated as compositions according to tables 6 and 7. Compounds and the mixtures from table 1 are labelled as “compound A” in table 6 and 7.

[0516] Table 6: Compositions 1A and 1 B

[0517] Table 7: Compositions 2A and 2B

[0518] M / BASFTR-2475-PC 230961W001

[0519] 58

[0520] Composition according to table 6 and table 7, namely 1A, 1 B, 2A, 2B, as well as the compositions of Tables 2, 3, 4 and 5 could be included in various compositions selected from the group consisting of Deo pump spray, Clean hair-conditioner, Face wash gel, Foam bath concentrate, Hair gel, Self-foaming bodywash, Sprayable sun care emulsion, Sprayable sun protection emulsion, Emollient facial gel, 2-phases oil foam bath, Shampoos, Shower bath, Hydro-alcoholic AP / Deo pump spray, Aerosol, Aqueous / alcoholic AP / Deo roll-on, Styling Gel Type "Out of Bed", Shaving Foam, Sensitive skin Baby shampoo, Body wash for Sensitive Skin, Gloss Enhancing Shampoo for Sensitive Scalp, Deo Stick, Baby Wipe, After shave balm, Face Gel, Face Day Care Cream, Face Cleanser, Body lotion, Sun Care SPF50+, Sprayable Lotion, Hand dish cleaner - regular, Hand dish cleaner - concentrate, Sanitary cleaner - concentrate, All-purpose cleaner, Anti-bacterial fabric softener, Detergent composition, Powder detergent composition and Liquid detergent composition.

[0521] A person skilled in art may be well versed with the various general formulations for the above-mentioned products.

[0522] Compositions 1 A, 1 B, 2A and 2B as well as the compositions of Tables 2, 3, 4 and 5 can for example be formulated in specific formulations as disclosed in IP.com Number: IPCGM000258614D entitled New Aroma Chemicals pages 6 to 46, Table 1 to Table D13, wherein the “Fragrance Composition 1A” is replaced by identical amounts of compositions 1A, 1 B, 2A or 2B.

[0523] M / BASFTR-2475-PC

Claims

230961W00159Claims1. A compound of formulaor a stereoisomer thereof or mixture of stereoisomers thereof.

2. The compound according to claim 1, which is present as the Z isomer or as a mixture of the Z and the E isomer, wherein the Z isomer is present in an amount of >50%, preferably of at least 80%, more preferably of at least 90%, in particular of at least 93%, specifically of at least 95%, relative to the total amount of the E and the Z isomer.

3. A mixture comprising- the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof according to any of claims 1 or 2; and- the compound of formula (II)or a stereoisomer thereof or a mixture of stereoisomers thereof.

4. The mixture according to claim 3, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1 : 10000 to 10000: 1 , preferably from 1 : 10000 to 1 : 10, more preferably from 1 :2000 to 1 :40, even more preferably from 1:1000 to 1 :50.

5. The mixture according to claim 4, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof and the compound of formula (II) or the stereoisomer thereof or the mixture of stereoisomers thereof are present in a weight ratio of from 1:500 to 1:90, preferably from 1 :450 to 1:95.

6. Use of the compound of formula (I) or of a stereoisomer thereof or of a mixture of stereoisomers thereof as defined in any of claims 1 or 2, for boosting or modifying theM / BASFTR-2475-PC230961W00160 aroma of the compound of formula (II) or of a stereoisomer thereof or of a mixture of stereoisomers thereof as defined in claim 3.

7. The use according to claim 6, for boosting or modifying the fragrance of the compound of formula (II) or of a stereoisomer thereof or of a mixture of stereoisomers thereof8. Use of the compound of formula (I) or of a stereoisomer thereof or of a mixture of stereoisomers thereof as defined in any of claims 1 or 2, or of the mixture as defined in any of claims 3 to 5, as an aroma chemical or to impart an aroma impression to a composition.

9. The use according to claim 8, as a fragrance or to impart a fragrance to a composition.

10. A method of imparting an aroma impression to a composition, comprising at least the step of adding the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of claims 1 or 2, or the mixture as defined in any of claims 3 to 5, to a composition; or comprising mixing simultaneously or consecutively the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of claims 1 or 2, or the mixture as defined in any of claims 3 to 5, with the other components of said composition or with pre-formed mixtures of a part of the other components of said composition.

11. The use or method according to claim 8 to 10, wherein in case that the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of claims 1 or 2 is used, the aroma impression is selected from the group consisting of floral violet note, fruity note, marine note, technical metallic note and any combination of two or more of these notes.

12. The use or method according any of the claims 8 to 11 , wherein the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of claims 1 or 2, or the mixture as defined in any of claims 3 to 5 is present in the composition in a total amount in the range of from 0.001 to 99.9% by weight, preferably from 0.005 to 90% by weight, more preferably from 0.01 to 80% by weight, in particular from 0.01 to 60% by weight, more particularly from 0.01 to 40% by weight, e.g. from 0.01 to 10% by weight or 0.01 to 7% by weight, based on the total weight of the composition.

13. A composition comprising the compound of formula (I) or a stereoisomer thereof or a mixture of stereoisomers thereof as defined in any of claims 1 or 2, or a mixture as defined in any of claims 3 to 5, and(i) at least one aroma chemical (X) other than compounds of formula (I) and (II) or(ii) at least one non-aroma chemical carrier, orM / BASFTR-2475-PC230961W00161(iii) both of (i) and (ii).

14. The composition according to claim 13, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of claims 1 or 2, or the mixture as defined in any of claims 3 to 5, is present in a total amount in the range of from 0.001 to 99.9% by weight, preferably from 0.005 to 90% by weight, more preferably from 0.01 to 80% by weight, in particular from 0.01 to 60% by weight, more particularly from 0.01 to 40% by weight, based on the total weight of the composition.

15. The composition according to claim 14, wherein the compound of formula (I) or the stereoisomer thereof or the mixture of stereoisomers thereof as defined in any of claims 1 or 2, or the mixture as defined in any of claims 3 to 5, is present in a total amount in the range of from 0.01 to 10% by weight, preferably from 0.01 to 7% by weight, based on the total weight of the composition.

16. The composition according to any of claims 13 to 15, wherein the at least one nonaroma chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant-active agents, or solvents.

17. The composition according to any of claims 13 to 16, comprising at least one aroma chemical (X) different from the compounds of formula (I) and (II) and optionally at least one non-aroma chemical carrier, where the at least one aroma chemical (X) different from the compounds of formula (I) and (II) is selected from the group consisting of: 2,6,10-trimethyl-9-undecenal (Adoxal), 3a,4,5,6,7,7a-hexahydro-1H-4,7- methanoinden-6-yl acetate (verdyl acetate), dodecanal (aldehyde C-12 (lauric)), 2- methylundecanal (aldehyde C12 MNA), aldehyde C-14 (gamma-undecalactone; 1 ,4- undecanolide), cyclamen aldehyde (2-methyl-3-(4-isobutylphenyl)-propanal), ambrocenide ((4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4h-4a,9- methanoazuleno(5,6-d)-1 ,3-dioxole), benzyl acetate, beta-ionone, isoamyl butyrate, calone (calone 1951, watermelon ketone, 7-methylbenzo[b][1,4]dioxepin-3-one), cetalox (naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-), cis-3-hexenyl isobutyrate, corps cassis, dartanol (also known as bacdanol, sandolene, topanzol or 2- ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), dupical (4-(octahydro-4,7- methano-5H-inden-5-ylidene)butanal), ethyl maltol (2 ethyl-3-hydroxy-4H-pyran-4- one), ethyl vanillin (4-hydroxy-3-ethoxybenzaldehyde), floralozone (florone, florazon, 3- (4-ethylphenyl)-2,2-dimethylpropanal), galbascone (dynascone; 1-(5,5-dimethyl-1 cyclo_'hexen-1-yl)-4-penten-1-one), gamma-decalactone (1,4-decanolide), gammaoctalactone (4-octanolide), geranyl acetate, habanolide (trans- 11-pentadecen- 1,15- olide; cis and trans-12-pentadecen-1, 15-olide), allyl heptanoate, hexyl acetate, indol, Iso E Super, isobutyl quinoleine, isoeugenol, javanol, lemonile, limette distillee, manzanate (ethyl 2-methylpentanoate), delta-muscenone, oxane, peonile, prenylM / BASFTR-2475-PC230961W00162 acetate, cis-3-hexenyl acetate, cis-3-hexenyl salicylate, isoamyl salicylate, stemone, tetrahdrolinalool, triplal (ligustral; vertocitral; trivertal; 2,4-dimethyl-3- cyclohexenecarbox-aldehyde), undecavertol (4-methyl-3-decen-5-ol), verdox (OTBCH, 2-tert-butylcyclohexyl acetate), violettyne (1,3-undecadien-5-yne), allyl 3- cyclohexylpropionate, allyl heptylate, ambroxide (ambrox; ambroxan; 3a, 6, 6, 9a tetramethyldodecahydronaphtho_'[2,1-b]furan), bacdanol (topanzol; sandolen; 2-ethyl- 4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), citronellyl acetate, cyclopentadecanolide (15-pentadecanolacton), damascenone, dihydromyrcenol, dimethyl benzyl carbinyl butyrate (alpha, alpha-dimethylphenylethyl butyrate), ethyl butyrate, ethyl maltol, ethyl 2-methylbutyrate, evernyl (methyl 2,4-dihydroxy-3,6- dimethylbenzoate), fructalate, hedione, hexyl isobutyrate, isoamyl acetate, methyl benzoate, methyl propyl oxathiane, para-cresyl methyl ether, phenoxyethyl isobutyrate, phenylethyl alcohol, pyranol (florol; 2-isobutyl-4-methyltetrahydro-2H pyran-4-ol), verdyl propionate (3a,4,5,6,7,7a-hexahydro-4,7-methano-1 H-inden-5(6)-yl propionate), 8-mercapto-menthanone, aldehyde C-18 (gamma-nonalactone; 5-pentyloxolan-2-one), alpha-ionone, citronellyl nitrile, cyclabute (tricyclodecenyl isobutyrate; 3a, 4, 5, 6, 7,7a- hexahydro-4,7-methano-1 H-inden-5(6)-yl isobutyrate), alpha-damascone, helvetolide, hexyl salicylate, hydratropic aldehyde dimethyl acetal (2-phenylpropionaldehyde dimethyl acetal), limonene, linalyl acetate, melonal, orange oil, para-menthenethiol, styrallyl acetate (1 -phenylethyl acetate), terpenyl acetate, hydroxycitronellal, amylvinylcarbinol (1-octen-3-ol), camphor, ethyl linalool, eucalyptol (cineol), hexyl butyrate, hexyl caproate (hexyl hexanoate), isoborneol, linalool oxide (2-(5-methyl-5- vinyltetrahydro-1-furyl)-2-propanol), methyl hexyl ketone (2-octanone), methyl octalactone (whisky lactone, 3-methyl-4-octanolide, 3-methyl-1,4-octanolide, 5-butyl-4- methyloxolan-2-one), ocimene, octyl acetate, terpineol alpha, terpinolene, terpinly acetate, para-cymene (1-methyl-4-(propan-2-yl)benzene, 4-isopropyltoluene) and mixtures thereof.

18. The composition according to any of the claims 13 to 17, wherein the composition is selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

19. A process for synthesizing the compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof as defined in any of claims 1 or 2, comprising at least the steps of a) acetylation of a compound of formula (III)M / BASFTR-2475-PC230961W00163 to form the compound of formula (I), and b) optionally purifying the compound of formula (I) obtained in step a).M / BASFTR-2475-PC

Images