Dodecadien-1-ol and dodecen-1-ol or mixtures thereof as aroma chemicals

Abstract

The present invention relates to dodecadien-1-ol, dodecene-1-ol or a mixture thereof and a preparation method thereof, and relates to use of dodecadien-1-ol, dodecene-1-ol or a mixture thereof as aromatic chemicals; relates to use of dodecene-1-ol and dodecene-1-ol or a mixture thereof for preparing an aromatic chemical composition or for changing the aromatic properties of an aromatic chemical composition; relates to an aromatic chemical composition comprising dodecane-1-ol, dodecene-1-ol or a mixture thereof; and relates to a method for preparing a perfuming composition or changing the aromatic properties of a perfuming composition.

Description

[0001] The present invention relates to dodecadien-1-ol and dodecene-1-ol or a mixture thereof and a preparation method thereof, and relates to the use of dodecadien-1-ol and dodecene-1-ol or a mixture thereof as aromatic chemicals; relates to the use of dodecadien-1-ol and dodecene-1-ol or a mixture thereof for preparing an aromatic chemical composition or for changing the aromatic properties of an aromatic chemical composition; relates to an aromatic chemical composition comprising dodecadien-1-ol and dodecene-1-ol or a mixture thereof; and relates to a method for preparing a perfuming composition or changing the aromatic properties of a perfuming composition. Technical Background

[0002] Aroma chemicals, especially fragrances, are of particular interest in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, are often in limited supply, and their content, purity, etc., also vary due to fluctuating environmental conditions. In order to circumvent these undesirable factors, it is therefore of great interest to produce synthetic substances that have organoleptic properties similar to those of more expensive natural fragrances or that have novel and interesting organoleptic properties.

[0003] Despite the existence of a large number of synthetic aromachemicals (flavors and fragrances), there is a constant need for new components that are able to meet the numerous properties required for extremely diverse fields of application. These include, firstly, organoleptic properties, i.e. the compounds should have favorable odor (olfactory) or taste properties. In addition, aromachemicals should also have further positive secondary properties, such as efficient preparation methods, the possibility of providing better sensory attributes due to synergistic effects with other flavors, higher stability under certain application conditions, higher scalability, better robustness, etc.

[0004] There is an increasing demand for aroma chemicals that can impart a fragrance impression to a composition, especially a woody / fruity / sweet / dried fruit / flower / iris / powdery / food-like odor impression. Such properties are particularly important for compositions, such as body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, and compositions for fragrance dispensers. Of particular interest are aroma chemicals that can impart one or more unique fragrance impressions to the composition, thereby contributing to a rich and interesting sensory profile, especially the olfactory profile of the composition. In addition, especially with regard to aroma chemicals that can impart a fragrance impression, firmness and persistence are particularly important in order to obtain a lasting odor impression in the composition and on the surface treated with the composition.

[0005] However, the targeted search for substances with specific organoleptic properties, such as a specific odor, is extremely difficult, since even small changes in the chemical structure can lead to large changes in organoleptic properties, such as odor and taste. The search for new flavors and fragrances is therefore in most cases difficult and laborious, without even knowing whether a substance with the desired odor and / or taste will actually be found.

[0006] It is an object of the present invention to provide new aroma chemicals. These should have pleasant organoleptic properties.

[0007] Another object of the present invention is to provide substances which can be used as aroma chemicals in ready-to-use compositions, in particular strongly odoriferous substances with a pleasant odor are sought. Furthermore, they should be usable in combination with other aroma chemicals, thereby creating novel advantageous sensory properties. Furthermore, these aroma chemicals should be obtainable from readily available starting substances, so that they can be produced quickly and economically.

[0008] This object is achieved by providing novel compounds of dodecadien-1-ol or dodecen-1-ol or mixtures thereof. The inventors have found that these compounds and / or mixtures have a pleasant odor, which reminds one of an impression selected from the group consisting of aldehyde notes, fatty notes, citrus notes, clean linen notes, floral notes, marine notes, orange notes, metallic notes, waxy notes and green notes. SUMMARY OF THE INVENTION

[0010] Therefore, a first aspect of the present invention relates to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol for imparting a fragrance impression to a composition.

[0011] In particular, compounds selected from dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol are used to impart a fragrance impression to the composition.

[0012] A second aspect of the invention relates to a method for imparting a fragrance impression to a composition, which comprises at least adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol.

[0013] In particular, the method of imparting a fragrance impression to a composition comprises at least adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol.

[0014] A third aspect of the present invention relates to a mixture comprising:

[0015] a) at least one selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and dodeca-

[0016] -4,11-diene-1-ol compounds; and

[0017] b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol; and

[0018] c) Dodecan-1-ol.

[0019] A fourth aspect of the present invention relates to an aroma chemical composition comprising a compound / mixture of the present invention and (i) at least one additional aroma chemical different from the compound of the present invention, or (ii) at least one non-aroma chemical carrier, or (iii) a mixture of (i) and (ii).

[0020] A fifth aspect of the present invention relates to the use of the compounds / mixtures of the present invention for preparing aroma chemical compositions.

[0021] A sixth aspect of the present invention relates to the use of the compounds / mixtures of the present invention for modifying the aroma properties of an aroma chemical composition.

[0022] The seventh aspect of the present invention relates to a method for preparing the compound of the present invention.

[0023] The eighth aspect of the present invention relates to a method for preparing an aroma chemical composition, which comprises the step of mixing the compound of the present invention with other ingredients such as at least one other aroma chemical and / or at least one non-aroma chemical carrier to obtain the aroma chemical composition.

[0024] The ninth aspect of the present invention relates to a method for changing the fragrance of an aroma chemical composition, which comprises the step of incorporating the compound of the present invention into the aroma chemical composition to obtain an aroma chemical composition with a changed fragrance.

[0025] The tenth aspect of the present invention relates to a method for modifying the aroma of a ready-to-use composition. The method comprises the step of incorporating a compound of the present invention into the ready-to-use composition to obtain a ready-to-use composition with modified aroma.

[0026] The compounds of the present invention and their aromachemical compositions have favorable sensory properties, especially pleasant fragrance. Therefore, they can be advantageously used as perfumery ingredients in perfume compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions, crop protection compositions and other ready-to-use compositions.

[0027] The pleasant fragrance, low volatility and excellent solubility make the compounds of the present invention suitable ingredients in compositions requiring a pleasant fragrance. Due to their physical properties, the compounds of the present invention can be well combined with other aroma chemicals and conventional ingredients in perfuming ready-to-use compositions, such as, in particular, perfume compositions. This allows, for example, the creation of fragrance compositions, in particular perfume compositions, having new advantageous organoleptic properties.

[0028] Furthermore, the compounds of the present invention can be prepared in good yield and purity by simple synthesis starting from readily available starting materials.Therefore, the compounds of the present invention can be prepared on a large scale in a simple and cost-effective manner. DETAILED DESCRIPTION OF THE INVENTION

[0030] The following detailed description is merely exemplary in nature and is not intended to limit the invention or the application and uses of the 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.

[0031] As used herein, the terms "comprising," "comprises," and "comprised of" are synonymous with "including," "includes," or "containing," "contains," and are inclusive or open-ended and do not exclude additional undescribed elements, components, or method steps. It should be understood that the terms "comprising," "comprises," and "comprised of" as used herein include the terms "consisting of," "consists," and "consists of."

[0032] In addition, the terms "(a)", "(b)", "(c)", "(d)", etc. in the specification and claims are used to distinguish similar elements and are not necessarily used to describe an order or chronological sequence. It should be understood that the terms so used are interchangeable where appropriate and that the embodiments of the subject matter described herein are capable of operating in other sequences than those described or illustrated herein. In the case of the terms "(A)", "(B)" and "(C)" or AA), BB) and CC) or "(a)", "(b)", "(c)", "(d)", "(i)", "(ii)", etc. referring to steps of a method or use or an assay, there is no temporal or temporal coherence between the steps, i.e., the steps may be performed 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 described above or below.

[0033] In the following paragraphs, different aspects of the subject matter are defined in more detail. Each aspect so defined can be combined with any other aspect or aspects, unless explicitly stated to the contrary. In particular, any feature indicated as being preferred or advantageous can be combined with any other feature or features indicated as being preferred or advantageous.

[0034] References throughout the specification to "one embodiment" or "embodiment" or "preferred embodiment" mean that a particular feature, structure, or characteristic described in conjunction with that embodiment is included in at least one embodiment of the present invention. Therefore, the phrases "in one embodiment" or "in preferred embodiments" appearing in various places throughout this specification do not necessarily all refer to the same embodiment, but may refer to the same embodiment. In addition, features, structures, or characteristics may be combined in one or more embodiments in any suitable manner, as those skilled in the art will appreciate from this disclosure. In addition, although some embodiments described herein include some other features that are not included in other embodiments, the combination of features of different embodiments is meant to be within the scope of the subject matter and to form different embodiments, as those skilled in the art will appreciate. For example, in the appended claims, any claimed embodiment is used in any combination.

[0035] In addition, ranges defined throughout the specification also include the endpoints, i.e., a range of 1-10 means that both 1 and 10 are included in the range. For the avoidance of doubt, the applicant shall be entitled to any equivalent solutions under applicable law.

[0036] definition

[0037] In the context of the present invention, the term "aroma" refers to a sensory property and includes smell and / or flavor.

[0038] The term "aromachemical" means a substance used to obtain a sensory or organoleptic (used interchangeably herein) impression, and includes its use for obtaining an olfactory and / or flavor impression. The term "olfactory impression" means an odor impression without any positive or negative judgment, while the term "fragrance impression" or "aroma impression" or "fragrance impression" (used interchangeably herein) is related to an overall pleasant odor impression. Thus, "flavor" or "fragrance" means an aromachemical that primarily causes a pleasant odor impression. Flavors cause taste impressions.

[0039] The term "fragrance composition" as used herein refers to a composition that causes an aroma. The term "fragrance composition" includes "odor composition" and / or "flavor composition". An odor composition is a composition that primarily causes an odor impression, and a flavor composition is a composition that primarily causes a taste impression.

[0040] The term "odor composition" includes "fragrance compositions" or "fragrance compositions" (used interchangeably herein) which predominantly evoke an odor impression which is generally perceived as pleasant.

[0041] The general hedonic expressions "favorable sensory properties" or "favorable organoleptic properties" describe the niceness and conciseness of the sensory impression presented by the fragrance chemical. "Niceness" and "conciseness" are terms familiar to the person skilled in the art, for example perfumers. Niceness generally refers to a pleasant sensory impression that is spontaneously evoked, brings about a positive perception. However, "niceness" is not necessarily synonymous with "sweetness". "Niceness" can also be the smell of musk or sandalwood. "Conciseness" generally refers to a spontaneously evoked sensory impression that reproducibly reminds the same specific thing for the same test panel. For example, a substance can have an odor that spontaneously reminds of "apple": the odor is then concisely "apple". If this apple odor is very pleasant, because the odor reminds of, for example, a sweet, fully ripe apple, the odor is called "nice". However, the odor of sour apples is also usually concise. If these two reactions occur simultaneously when smelling the substance, in this example, it is therefore a nice and concise apple odor, then this substance has particularly favorable sensory properties.

[0042] When used herein to refer to a composition, method or use of two compounds, the expression "combined", "combined with" or "combined together" takes into account the fact that the two compounds are not necessarily used in the form of a physical mixture of the compounds, but can be used separately (e.g., added). In the case of separate use of the compounds, they can be used (e.g., added) sequentially (i.e., one after the other) in any order, or used simultaneously (i.e., substantially simultaneously).

[0043] The term "enhancement" is used herein to describe the effect of enhancing and / or modifying the scent of a fragrance chemical or composition. The term "enhancement" includes an improvement in the niceness and / or simplicity of a scent and / or an improvement in intensity. The term "modification" includes a change in the scent attributes.

[0044] Intensity can be determined by threshold determination. The threshold of an odor is the concentration of a substance in the relevant gas space at which a representative test panel can still perceive the odor impression, although it no longer needs to be defined.

[0045] The enhanced effect of perfume compositions is particularly desirable when a top note character is desired in applications where the odor is to be delivered particularly quickly and intensely, for example in the taste area of ​​deodorants, air fresheners or chewing gum.

[0046] The terms "the present invention relates to" and "the present invention is directed to" are used synonymously throughout the present invention.

[0047] The terms "compound" and "substance" are used synonymously throughout the present invention.

[0048] The term "lasting power" describes the evaporation behavior of an aroma chemical over time. The lasting power can be determined, for example, 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 lasting power, the time span over which the test panel can still recognize the fragrance impression is long.

[0049] The term "fastness" describes the interaction of fragrance chemicals with surfaces such as skin or fabrics, especially after subsequent treatment of the surface such as washing. Fastness can be determined, for example, by washing fabrics with a fabric detergent composition comprising a fragrance chemical and then performing an olfactory evaluation of the fabrics directly after washing (wet fabrics) and evaluating dry fabrics after prolonged storage.

[0050] The term "stability" describes the behavior of an aroma chemical when in contact with oxygen, light and / or other substances. An aroma chemical with high stability retains its fragrance attributes over a long period of time, preferably in a variety of compositions and under various storage conditions.

[0051] In order to impart a long-lasting fragrance impression to the composition or to a surface treated with the composition, the persistence, firmness and stability of the fragrance chemicals in the composition should preferably be high.

[0052] Unless otherwise indicated herein, the names of "compounds" and non-stereospecific compounds described herein, such as "4,8-dodecadien-1-ol", are not limited to any specific stereoisomer or specific mixture of stereoisomers. Therefore, the compound of the present invention can be a single stereoisomer of 4,8-dodecadien-1-ol selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol; or it can be a mixture of two or more of these stereoisomers of 4,8-dodecadien-1-ol.

[0053] Compound:

[0054] One embodiment of the present invention relates to a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol.

[0055] In a preferred embodiment, the compound is selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol.

[0056] In another embodiment of the present invention, the compound of the present invention may be a single stereoisomer selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E)dodec-4,11-dien-1-ol, (4Z)dodec-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol.

[0057] Preferably, the compound of the present invention may be a single stereoisomer selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E)dodec-4,11-dien-1-ol, (4Z)dodec-4,11-dien-1-ol.

[0058] mixture

[0059] In yet another embodiment, the present invention relates to a mixture comprising:

[0060] a) at least one selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and dodeca-

[0061] -4,11-diene-1-ol compounds; and

[0062] b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.

[0063] In yet another embodiment of the present invention, dodeca-4,8-dien-1-ol is selected from the group consisting of (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol.

[0064] In yet another embodiment of the present invention, dodeca-8,11-dien-1-ol is selected from the group consisting of (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0065] In yet another embodiment of the present invention, dodeca-4,11-dien-1-ol is selected from the group consisting of (4E) dodeca-4,11-dien-1-ol and (4Z) dodeca-4,11-dien-1-ol.

[0066] In yet another embodiment of the present invention, 4-dodecen-1-ol is selected from the group consisting of (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0067] In another embodiment of the present invention, 8-dodecen-1-ol is selected from the group consisting of (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0068] In an embodiment of the present invention, the mixture further comprises dodecan-1-ol.

[0069] use:

[0070] One embodiment of the present invention relates to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol for imparting a fragrance impression to a composition.

[0071] Preferably, the present invention relates to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0072] In an embodiment of the present invention, a compound selected from the group consisting of (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E) dodec-4,11-dien-1-ol, (4Z) dodec-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol can be used as an aroma chemical.

[0073] Preferably, compounds selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E)dodec-4,11-dien-1-ol, (4Z)dodec-4,11-dien-1-ol can be used as aroma chemicals.

[0074] In an embodiment of the present invention, the compound / mixture of the present invention or an aroma chemical composition comprising the compound / mixture is used as a fragrance.

[0075] In particular, the compounds of the invention are used to impart fragrance notes reminiscent of aldehyde notes, fatty notes, citrus notes, clean linen notes, floral notes, marine notes, mandarin notes, metallic notes, waxy notes, violet leaves and green notes.

[0076] The compounds / mixtures according to the invention can be used in ready-to-use compositions in general, in particular in perfumed ready-to-use compositions. "Perfumed ready-to-use compositions" as used herein refer to ready-to-use compositions which primarily give rise to a pleasant odor and / or taste impression. In a preferred embodiment, the perfumed ready-to-use composition is a scented ready-to-use composition, i.e. produces a pleasant odor.

[0077] Scented, ready-to-use compositions are, for example, compositions for personal care, home care, industrial applications and also compositions for other applications, such as pharmaceutical compositions or crop protection compositions.

[0078] Preferably, the compounds of the present invention are used in a composition selected from perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions. The compounds of the present invention are used as aroma chemicals in the above compositions, preferably as fragrances.

[0079] In particular, the compounds of the invention are used to impart a fragrance reminiscent of dried fruits, floral notes, candies, irises, powdery notes; or to produce a fragrance reminiscent of candies, floral notes, fruity notes for the above-mentioned compositions.

[0080] Details of the above compositions are given below.

[0081] Similarly, due to the synergistic effect with other aroma chemicals (e.g., other flavors) contained in the composition, the compounds of the present invention can improve the sensory attributes of the aroma chemical composition, which means that the compounds can provide a boosting effect for other aroma chemicals. Therefore, the compounds are suitable as enhancers for other aroma chemicals.

[0082] Therefore, the present invention also relates to the use of the compounds according to the invention for modifying the aroma profile (eg fragrance profile) of a perfuming (eg fragranced) composition; in particular as enhancers for other aroma chemicals.

[0083] The enhancing effect of a substance means that the substance in an aromachemical formulation (e.g., a perfume formulation) strengthens and intensifies the overall sensory (e.g., olfactory) impression of the formulation. For example, in the case of mint, it is known that menthyl methyl ether strengthens the aroma or flavoring mixture of mint oil, especially in the top notes, bringing about a significantly stronger and more complex sensation, although the ether itself, as a pure substance, does not produce a particularly strong odor at all. In perfume applications, as a pure substance, it only exhibits a light jasmine note. (Methyl dihydrojasmonate) as an odor enhancer enhances the spread, freshness and volume of perfume compositions. The enhancement effect is particularly desirable when a top note character is desired in applications where the odor impression is to be delivered particularly quickly and intensely, such as in deodorants, air fresheners or in the taste field in chewing gum.

[0084] To achieve this enhancement, the compounds of the present invention can be used, for example, in an amount of 0.001-10 wt.%, such as 0.01-2 wt.%, preferably 0.05-1 wt.%, especially 0.1-0.5 wt.%, based on the total weight of the resulting aromachemical composition.

[0085] In addition, the compounds of the present invention can have further positive effects on the composition in which it is used. For example, the compounds can enhance the overall performance of the composition into which it is incorporated, such as the stability of the composition, such as formulation stability, scalability or durability.

[0086] method:

[0087] Dodecadien-1-ol and dodecene-1-ol or mixtures thereof can be prepared by standard methods of organic chemistry and by methods described in the prior art. More precisely, dodecadien-1-ol and dodecene-1-ol or mixtures thereof can be prepared by hydrogenating 4,8,11-dodecatrienal to form dodecadien-1-ol and dodecene-1-ol or mixtures thereof. Specifically, we obtain 4,8-dodecadien-1-ol and a mixture of 4-dodecadien-1-ol and 8-dodecadien-1-ol as cis / trans isomers.

[0088] The reaction can be carried out, for example, in analogy to the method described in Liebigs Annalen der Chemie (1982), (8), 1478-94.

[0089] In an embodiment, different ratios of the corresponding alcohols can be determined by H-NMR (olefin:methylene), depending on the hydrogenation time.

[0090] In an embodiment, the catalyst used in the reaction is selected from ruthenium, iridium, rhodium, platinum, palladium.

[0091] In an embodiment, the reaction is carried out at a temperature of 50-70°C, preferably 50-65°C, more preferably 50-60°C.

[0092] In an embodiment, the reaction is carried out at a pressure of 25-40 bar, preferably 25-35 bar, more preferably 25-30 bar.

[0093] In embodiments, the reaction is carried out for 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, 6 hours, 7 hours, 18 hours, 19 hours, 20 hours.

[0094] In an embodiment of the present invention, a tertiary amine is used as a catalyst / activator in the reaction. Tri-n-alkylamines are preferred, especially triethylamine, tri-n-propylamine, tri-n-butylamine and trimethylamine.

[0095] In the embodiment, 4,8,11-dodecatrienal (1.2 kg, 82 mmol) is dissolved in methanol (800 g) in a 3.5 L autoclave in the presence of trimethylamine (48 g, 3 wt.%) and Ru / Fe-based catalyst (20 g, 1,6 wt.%). The hydrogenation reaction is carried out at T=55° C. and 30 bar of hydrogen pressure to produce 4,8-dodecadien-1-ol as well as 4-dodecadien-1-ol and 8-dodecadien-1-ol as cis / trans isomers.

[0096] In the embodiment, the reaction time is 6 hours, and the percentages of dodecenol and dodecadienol obtained are 12% and 88%, respectively.

[0097] In yet another embodiment, the reaction time is 8 hours, and the percentages of dodecenol and dodecadienol obtained are 40% and 60%, respectively.

[0098] In another embodiment, the reaction time is 14 hours, and the percentages of dodecenol and dodecadienol obtained are 66% and 34%, respectively.

[0099] Composition:

[0100] In an embodiment, the present invention relates to an aroma chemical composition comprising a compound / mixture of the present invention, and

[0101] (i) at least one additional aroma chemical, or

[0102] (ii) at least one non-aroma chemical carrier, or

[0103] (iii) Both (i) and (ii).

[0104] As used herein, the term "fragrance chemical composition" refers to a composition that induces a pleasant fragrance, such as a pleasant odor impression.

[0105] Particularly, the non-aromatic chemical carrier in the aroma chemical composition of the present invention may be selected from surfactants, oil components and solvents.

[0106] The additional aroma chemicals are different from the compounds / mixtures of the present invention.

[0107] Due to their physical properties, the compounds / mixtures can be well combined with other aroma chemicals (e.g. other flavors) and other conventional ingredients in perfuming (e.g., scenting) ready-to-use compositions, such as, in particular, perfume compositions. This allows, for example, the creation of fragrance compositions (e.g., perfume compositions) with novel advantageous sensory attributes. In particular, as described above, the compounds can provide a boosting effect to other aroma chemicals (e.g., other flavors).

[0108] Thus, in a preferred embodiment, the aroma chemical composition comprises a compound of the invention as defined herein and at least one additional aroma chemical different from a compound / mixture of the invention.

[0109] The additional aroma chemical may be, for example, one, preferably 2, 3, 4, 5, 6, 7, 8 or further other aroma chemicals selected from:

[0110] Geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopentadien[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methylene-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellol acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styroyl acetate, octahydro- 2,3,8,8-tetramethyl-2-naphthyl acetonide and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butyl cyclohexyl acetate, 2-tert-butyl cyclohexyl acetate, α-ionone, n-α-methylionone, α-isomethylionone, coumarin, terpineol acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, α-amylcinnamaldehyde, brazilic acid ethylene glycol ester, (E)- and / or (Z)-3-methylcyclopentadecan-5-enone, 15-pentadecan-11-enelactone and / or 15-pentadecan-12-enelactone, 1 5-cyclopentadecalactone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)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-heptene-1-al, borneol, 3-(3-isopropylphenyl)butyraldehyde, 2-methyl-3-(3,4-methylenediamine)butyraldehyde 1,2-dimethylpropanal, 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]heptan-2-yl]cyclohexane-1-ol.

[0111] In yet another preferred embodiment, the at least one aroma chemical (i) is selected from 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.

[0112] In yet another preferred embodiment, the at least one aroma chemical (i) is selected from ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furanol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0113] Other aroma chemicals that can be combined with the compounds of the present invention to produce the compositions of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Vols. I and II, Montclair, NJ, 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th edition, Wiley-VCH, Weinheim 2001.

[0114] Specifically, we can mention:

[0115] Extracts from natural raw materials, such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, e.g.

[0116] Ambergris tincture; Balsam oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Moss absolute; Bay oil; Wormwood oil; Benzoin resin; Bergamot oil; Beeswax absolute; Birch tar; Bitter almond oil; Celery oil; Buchu leaf oil; Brazilian sandalwood oil; Juniper tar; Calamus oil; Camphor oil; Ylang ylang oil; Cardamom oil; Caraway oil; Cinnamon oil; Cinnamon absolute; Castoreum absolute; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronella oil; Lemon oil; Copaiba balsam; Copaiba balsam oil; Coriander oil; Costus root oil; Kumin oil; Cypress oil; Davana oil; Dill leaf oil; Dill seed oil; Eau de brouts absolute; oakmoss absolute; elemi resin oil; tarragon oil; lemon eucalyptus oil; eucalyptus oil; fennel oil; pine needle oil; galbanum oil; galbanum resin; geranium oil; grapefruit oil; guaiac wood oil; guarana resin; guarana balsam oil; helichrysum absolute; helichrysum oil; ginger oil; orris root absolute; orris root oil; jasmine absolute; sweet calamus oil; blue chamomile oil; Roman chamomile oil; carrot seed oil; quinoa oil; pine needle oil; spearmint Oil; Artemisia annua oil; Lavender oil; Lavender absolute; Lavender resin; Lavender absolute; Lavender oil; Lemongrass oil; Angelica dahurica oil; Lime oil distilled; Lime oil pressed; Camphor oil; Litsea cubeba oil; Bay leaf oil; Nutmeg oil; Origanum vulgare oil; Mandarin oil; Cinnamon bark oil; Mimosa absolute; Musk seed oil; Musk tincture; Sage oil; Nutmeg oil; Myrrh absolute; Myrrh Oil; Myrtle Oil; Clove Leaf Oil; Clove Flower Oil; Neroli Oil; Frankincense Absolute; Frankincense Oil; Red Myrrh Oil; Neroli Absolute; Orange Oil; Oregano Oil; Palmarosa Oil; Patchouli Oil; Perilla Seed Oil; Peru Balsam Oil; Parsley Leaf Oil; Parsley Seed Oil; Petitgrain Oil; Peppermint Oil; Pepper Oil; Allspice Seed Oil; Pine Oil; Peppermint Oil; Rose Absolute; Rosewood Oil; Rose Oil; Rosemary Oil; Sage Oil; Spanish Sage Oil ; sandalwood oil; celery seed oil; spike lavender oil; star anise oil; styrax oil; marigold oil; fir leaf oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka bean absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; lees oil; wormwood oil; wintergreen oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof, or components isolated therefrom;

[0117] Individual essences selected from hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;

[0118] Aliphatic alcohols, for example hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenols; 1-octen-3-ol; a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

[0119] Aliphatic aldehydes and acetals thereof, for example 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; heptenal diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyl acetaldehyde; (E / Z)-1-(1-methoxypropoxy)-hex-3-ene; aliphatic ketones and their oximes, for example 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;

[0120] Aliphatic sulfur compounds, such as 3-methylthiohexanol; 3-methylthiohexanol acetate; 3-mercaptohexanol; 3-mercaptohexanol acetate; 3-mercaptohexanol butyrate; 3-acetylthiohexanol acetate; 1-menthene-8-thiol;

[0121] Aliphatic nitriles, for example 2-nonenenitrile; 2-undecenenitrile; 2-tridecenenitrile; 3,12-tridecadienenitrile; 3,7-dimethyl-2,6-octadienenitrile; 3,7-dimethyl-6-octenenitrile;

[0122] Esters of aliphatic carboxylic acids, for example (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate ; (E)- and (Z)-3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octynoate; methyl 2-nonynoate; allyl 2-isopentyloxyacetate; methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

[0123] acyclic terpene alcohols, for example 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 their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0124] acyclic terpene aldehydes and ketones, such as geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; and the dimethyl- and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal; cyclic terpene alcohols, such as menthol; isopulegol; alpha-terpineol; terpine-4-ol; menth-8-ol; menth-1-ol; menth-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetivol; guaiacol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0125] Cyclic terpene aldehydes and ketones, for example menthone; isomenthone; 8-mercaptomenth-3-one; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-isomethylionone; β-isomethylionone; α-irone; α-damascone; β-damascone; β-damascone; δ-damascone; γ-damascone; 1-(2,4,4-trimethyl- 2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methylenenaphthalene-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; oleanone; dihydrooleanone; 4,6,8-megatrien-3-one; α-orangealdehyde; β-orangealdehyde; acetylated cedarwood oil (methyl cedarwood ketone);

[0126] Cyclic alcohols, for example 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isoborneolcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

[0127] Alicyclic alcohols, such as α-3,3-trimethylcyclohexylmethanol; 1-(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-butene-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-butene-1-ol; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-butene-1-ol; -(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;

[0128] Cyclic and alicyclic ethers, for example eucalyptol; cedarwood methyl ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedarwood oxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo-[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

[0129] Cyclic and macrocyclic ketones, for example 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-Methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecene-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclohexadecene-1-one; 7-cyclohexadecene-1-one; (7 / 8)-cyclohexadecene-1-one; 9-cycloheptadecene-1-one; cyclopentadecanone; cyclohexadecanone;

[0130] Cycloaliphatic aldehydes, for example 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarboxaldehyde;

[0131] Alicyclic ketones, for example 1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthylmethyl ketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl)ketone;

[0132] Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-amylcyclohexyl acetate; 4-tert-amylcyclohexyl 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 ester; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate; 4,7-methyleneoctahydro-5 or 6-indenyl acetate;

[0133] Esters of cycloaliphatic alcohols, for example 1-cyclohexylethyl crotonate;

[0134] Esters of cycloaliphatic carboxylic acids, for example allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; cis- and trans-methyl dihydrojasmonate; cis- and trans-methyl jasmonate; methyl 2-hexyl-3-oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl 2-methyl-1,3-dioxolane-2-acetate;

[0135] Aromatic aliphatic alcohols, for example benzyl alcohol; 1-phenylethanol, 2-phenylethanol, 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethanol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4-isopropylphenyl)ethanol;

[0136] Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, for example benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethylbenzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

[0137] Aromatic aliphatic ethers, for example 2-phenethyl methyl ether; 2-phenethyl isopentyl ether; 2-phenethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; 2-phenylpropanal dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetrahydroindenyl[1,2-d]-m-dioxane; 4,4a,5,9b-tetrahydro-2,4-dimethylindenyl[1,2-d]-m-dioxane;

[0138] Aromatic and aromatic aliphatic aldehydes, for example benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; 2-phenylpropanal; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert-butylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal; Cinnamaldehyde; α-butylcinnamaldehyde; α-amylcinnamaldehyde; α-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal;

[0139] Aromatic and araliphatic ketones, for example acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthyl)ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5′,6′,7′,8′-tetrahydro-3′,5′,5′,6′,8′,8′-hexamethyl-2-naphthylacetonone;

[0140] Aromatic and aliphatic carboxylic acids and their esters, for example benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isopentyl 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;

[0141] Nitrogen-containing aromatic compounds, for example 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-pentanenitrile; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; methyl N-methyl anthranilate; the Schiff base of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

[0142] Phenols, phenyl ethers and phenyl esters, for example estragole; anethole; eugenol; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether; β-naphthyl methyl ether; β-naphthyl ethyl ether; β-naphthyl isobutyl ether; 1,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresol phenylacetate;

[0143] Heterocyclic compounds, for example 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;

[0144] Lactones, such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decano-1,4-lactone; 1,4-undecalactone; 1,4-dodecalactone; 1,5-decanolide; 1,5-dodecalactone; 4-methyl-1,4-decanolide; 1,15-pentadecalactone; cis- and trans-11-pentadecene-1,15-lactone ; cis- and trans-12-pentadecen-1,15-lactone; 1,16-hexadecene-1,16-lactone; 9-hexadecene-1,16-lactone; 10-oxa-1,16-hexadecene-lactone; 11-oxa-1,16-hexadecene-lactone; 12-oxa-1,16-hexadecene-lactone; 1,12-dodecanediol glycol ester; 1,13-tridecanediol glycol ester; coumarin; 2,3-dihydrocoumarin; octahydrocoumarin.

[0145] In a preferred embodiment, the at least one non-fragrance chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant actives and solvents.

[0146] In the context of the present invention, a "solvent" is used to dilute the compound of the present invention and / or any other components of the composition used according to the present invention, without having a fragrance of its own.

[0147] The amount of solvent is selected according to the composition.

[0148] In another preferred embodiment, the solvent is selected from ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, triethyl citrate and isopropyl myristate.

[0149] In another preferred embodiment, the solvent is present in the composition in an amount of 0.01-99.0 wt.%, more preferably in an amount of 0.05-95.0 wt.%, still more preferably in an amount of 0.1-80.0 wt.%, most preferably 0.1-70.0 wt.%, and in particular in an amount of 0.1-60.0 wt.%, based on the total weight of the composition.

[0150] In another preferred embodiment of the present invention, the composition comprises 0.05-10 wt.%, more preferably 0.1-5 wt.%, still more preferably 0.2-3 wt.% of solvent, based on the total weight of the composition. In another preferred embodiment of the present invention, the composition comprises 20-70 wt.%, more preferably 25-50 wt.% of solvent, based on the total weight of the composition.

[0151] One embodiment of the present invention relates to a composition comprising a compound of the present invention and at least one oil component.

[0152] In a preferred embodiment, the oil component is present in an amount of 0.1-80 wt.%, more preferably 0.5-70 wt.%, still more preferably 1-60 wt.%, even more preferably 1-50 wt.%, particularly 1-40 wt.%, more particularly 5-25 wt.%, especially 5-15 wt.%, based on the total weight of the composition.

[0153] The oil component can be selected, for example, from Guerbet alcohols and other additional esters based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, 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, erucate, stearyl Suitable are stearyl myristate, isostearyl palmitate, isostearyl stearate, 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 C 18 -C 38 Alkyl hydroxycarboxylic acid with straight chain or branched C6-C 22 Esters of fatty alcohols, more particularly dioctyl malate, esters of linear and / or branched fatty acids with polyols (for example propylene glycol, dimer diol or trimer triol), based on C6-C 10 Triglycerides of fatty acids, based on C6-C 18 Liquid mixture of mono-, di- and triglycerides of fatty acids, C6-C 22 Esters of fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C 22 Fatty alcohol carbonates, such as dicaprylyl carbonate ( CC), Guerbet carbonates based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, benzoic acid esters and linear and / or branched C6-C 22 Esters of alcohols (e.g. TN), a linear or branched symmetrical or asymmetrical dialkyl ether having 6 to 22 carbon atoms in each alkyl group, such as dioctyl ether ( OE), ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof.

[0154] It is understood that antioxidants are capable of inhibiting or preventing undesirable changes in the composition to be protected caused by the action of oxygen and other oxidative processes. In most cases, antioxidants function in that they act as free radical scavengers of free radicals generated in the autooxidative process.

[0155] In a preferred embodiment, the antioxidant is selected from:

[0156] ●Amino acids (e.g. glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives,

[0157] Imidazoles (e.g. urocanic acid) and their derivatives,

[0158] Peptides, such as D,L-carnosine, D-carnosine, L-carnosine (=β-alanyl-L-histidine) and their derivatives,

[0159] ● Carotenoids, carotenes (e.g. α-carotene, β-carotene, lycopene, lutein) or their derivatives,

[0160] ●Chlorogenic acid and its derivatives,

[0161] ●Lipoic acid and its derivatives (such as dihydrolipoic acid),

[0162] Auro-thioglucose, propylthiouracil and other thiols (e.g., thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, pentyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts,

[0163] ● Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

[0164] ●Sulfoxide amine compounds (e.g., buthionine sulfoxide amine, homocysteine ​​sulfoxide amine, buthionine sulfone, pentylthionine sulfoxide amine, hexylthionine sulfoxide amine, heptylthionine sulfoxide amine),

[0165] ●(Metal) chelators (e.g. alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

[0166] Alpha-hydroxy acids (e.g., citric acid, lactic acid, malic acid),

[0167] Humic acid, bile acid, bile extract, bilirubin, biliverdin, boldine (= alkaloids from the plant Peumus boldus, boldus extract),

[0168] ●EDTA, EGTA and their derivatives,

[0169] ● Unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid, linoleic acid, oleic acid),

[0170] ●Folic acid and its derivatives,

[0171] ● Ubiquinone and ubiquinol and their derivatives,

[0172] Vitamin C and derivatives (e.g., ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

[0173] Tocopherol and derivatives (e.g. vitamin E acetate),

[0174] Vitamin A and its derivatives (e.g. vitamin A palmitate),

[0175] ● Benzoin gum coniferyl benzoate, rutin and its derivatives, α-glycosyl rutin, ferulic acid, furfurylidene glucitol,

[0176] ●Butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA),

[0177] ●nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives,

[0178] ●Superoxide dismutase,

[0179] ● Zinc and its derivatives (such as ZnO, ZnSO4),

[0180] Selenium and its derivatives (e.g. selenomethionine), and

[0181] ●Stilbene and its derivatives (eg, stilbene oxide, trans-stilbene oxide).

[0182] In a preferred embodiment, the antioxidant is selected from pentaerythritol tetra-di-tert-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate and tocopherol.

[0183] In another preferred embodiment, the composition of the present invention may contain 0.001-25wt.%, preferably 0.005-10wt.%, more preferably 0.01-8wt.%, still more preferably 0.025-7wt.%, even more preferably 0.05-5wt.% of antioxidant, based on the total weight of the composition.

[0184] Deodorizing compositions (deodorants and antiperspirants) counteract, mask or eliminate body odor. Body odor is formed by the action of skin bacteria on apocrine sweat, resulting in the formation of unpleasant-smelling degradation products.

[0185] Thus, one embodiment of the present invention relates to a composition comprising a compound of the present invention and at least one deodorant active. In a preferred embodiment, the deodorant active is selected from antiperspirants, esterase inhibitors and antimicrobial agents.

[0186] Suitable antiperspirants are selected from the salts of aluminum, zirconium or zinc. Examples are aluminum chloride, aluminum chlorohydrate, hydrated tetrahydroxyaluminum dichloro, hydrated 4.5-hydroxyaluminum sesquichloro and complex compounds thereof, for example complexes with 1,2-propylene glycol, aluminum hydroxyallantoate, aluminum chlorotartrate, hydrated tridecahydroxyaluminum zirconium trichloro, hydrated tetrachlorododechydroxyaluminum zirconium, hydrated tricoshydroxyaluminum zirconium pentachloro and complex compounds thereof, for example complex compounds of amino acids, such as glycine. Preference is given to using aluminum chlorohydrate, hydrated tetrachlorododechydroxyaluminum zirconium, hydrated tricoshydroxyaluminum zirconium pentachloro and complex compounds thereof.

[0187] In a preferred embodiment, the antiperspirant is selected from aluminum chloride, aluminum chlorohydrate, tetrahydroxyaluminum dichlorohydrate, 4.5-hydroxyaluminum sesquichlorohydrate, aluminum hydroxyallantoate, aluminum chlorotartrate, tridecahydroxyaluminum zirconium trichlorohydrate, tetrachlorododecanoic aluminum zirconium tetrahydrate, and tricoshydroxyaluminum zirconium pentachlorohydrate.

[0188] Where the underarm area sweats, bacteria form extracellular enzymes - esterases, mainly proteases and / or lipases, and decompose the esters present in the sweat, 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, thereby reducing the formation of odors. Free acids may be released by the cleavage of citrate esters and reduce the pH value of the skin, making the enzyme inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfates or phosphates, dicarboxylic acids and esters thereof, such as glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, such as citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.

[0189] In a preferred embodiment, 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, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartrate and zinc glycinate.

[0190] The composition of the present invention comprises 0.01-20 wt.%, preferably 0.1-10 wt.%, more particularly 0.5-5 wt.% of an esterase inhibitor, based on the total weight of the composition.

[0191] As used herein, the term "antimicrobial agent" includes substances having bactericidal and / or bacteriostatic properties. These substances are usually active against Gram-positive bacteria, for example 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynylbutylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glyceryl monocaprate, glyceryl monocaprylate, glyceryl monolaurate (GML), diglyceryl monocaprate (DMC), salicylic acid-N-alkylamides, for example salicylic acid n-octylamide or salicylic acid n-decylamide

[0192] In a preferred embodiment, the antimicrobial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3 -Methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glyceryl monocaprate, glyceryl monocaprylate, glyceryl monolaurate (GML), diglyceryl monocaprate (DMC), salicylic acid-N-alkylamide.

[0193] The composition of the present invention comprises 0.01-5 wt.%, preferably 0.1-2 wt.% of an antibacterial agent, based on the total weight of the composition.

[0194] In a preferred embodiment, the composition preferably comprises a surfactant. Due to the characteristic fragrance properties of the compound of the invention and its firmness, persistence and stability, it can be used in particular to provide a smell, preferably a fragrance impression or a fragrance impression to a composition containing a surfactant, such as a cleaning agent (in particular laundry care products and all-purpose cleaners). It can preferably be used to give a composition containing a surfactant a lasting floral and / or marine and / or green and / or sweet and / or rubber and / or nutty and / or woody and / or dusty and / or rooty and / or lemony odor impression.

[0195] In a preferred embodiment, the surfactant is selected from anionic, nonionic, cationic, amphoteric and zwitterionic surfactants. In yet another preferred embodiment, the surfactant is an anionic surfactant.

[0196] Therefore, the composition of the present invention may preferably contain at least one surfactant. The surfactant may be selected from anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants. Compositions containing surfactants, such as shower gels, foaming shower gels, shampoos, etc. preferably contain at least one anionic surfactant.

[0197] The composition of the present invention generally contains a surfactant in an amount of 0-40 wt.%, preferably 0-20 wt.%, more preferably 0.1-15 wt.%, in particular 0.1-10 wt.%, based on the total weight of the composition. Typical examples of 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 methylals, optionally partially oxidized alkyl (alkenyl) oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkylglucamides, protein hydrolysates (especially wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, although they preferably have a narrow range of homolog distribution.

[0198] Zwitterionic surfactants contain at least one quaternary ammonium group and at least one –COO (-) or –SO3 (-) Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinates, N-amidopropyl-N,N-dimethylammonium glycinates, for example cocoamidopropyldimethylammonium glycinates, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines, which contain 8 to 18 carbon atoms in the alkyl or acyl radical, and cocoamidoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivatives known by the CTFA name cocoamidopropyl betaine are particularly preferred.

[0199] Amphoteric surfactants are also suitable, especially as cosurfactants. 18A surface-active compound which, in addition to the alkyl or acyl radical, contains at least one free amino group and at least one -COOH- or -SO3H- group and is capable of forming internal salts. Examples of suitable amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, having approximately 8 to 18 carbon atoms in the alkyl radical. Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionates, cocoamidoethylaminopropionates and acylsarcosines.

[0200] Anionic surfactants are characterized by a water-soluble anionic group, such as a carboxylate, sulfate, sulfonate or phosphate group, and a lipophilic group. Skin-safe anionic surfactants are known to practitioners in large quantities from relevant textbooks and are commercially available. They are particularly alkyl sulfates (in the form of their alkali metal, ammonium or alkanolammonium salts), alkyl ether sulfates, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, linear C-containing anionic surfactants, and alkyl ether sulfates. 12-18 Alkyl or acyl acyltaurines, and sulfosuccinates and acylglutamates (in the form of their alkali metal or ammonium salts).

[0201] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more especially ammonium chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. In addition, readily biodegradable quaternary ammonium ester compounds, for example dialkylammonium methosulfates and methylhydroxyalkyldialkyloxyalkylammonium methosulfates sold under the name Stepantexe, and The corresponding products of the quaternary ammonium series can be used as cationic surfactants. "Esterquats" are generally understood to mean quaternized fatty acid triethanolamine ester salts. They can provide the composition with a particularly soft feel. They are known substances produced by relevant methods of organic chemistry. Other cationic surfactants that can be used according to the invention are quaternized protein hydrolysates.

[0202] One embodiment of the present invention relates to a composition selected from the group consisting of perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0203] The composition is preferably an aroma chemical composition, more preferably a perfume composition.

[0204] Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene preparations, cleaning compositions (including dishwashing compositions), fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0205] The fragrance composition may be chosen from fine fragrances, air fresheners in liquid form, gel form or in the form of an application to a solid carrier, aerosol sprays, scented cleansers, scented candles and oils, such as lamp oils or massage oils.

[0206] Examples of fine fragrances are perfume extracts, Eau de Parfums, Eau de Toilettes, Eau de Colognes, Eau de Solide and Extrait Parfum.

[0207] Body care compositions include cosmetic compositions and products for oral and dental hygiene and may be chosen from aftershave products, preshave products, splash colognes, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions, such as skin lotions, face lotions, sunscreen lotions, aftersun lotions, hand lotions, foot lotions, depilatory creams, aftershave lotions, self-tanning lotions, hair care products, such as hair sprays, hair gels, setting hair lotions, conditioners, shampoos, permanent and semi-permanent hair colorants, hair styling compositions such as cold waves and hair softening compositions, hair tonics, hair creams and hair lotions. lotions, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, decorative cosmetics, such as eyeliner, eye shadow, nail polish, make-up, lipstick and mascara.

[0208] Oral dental hygiene products include, for example, toothpaste, dental floss, mouthwash, breath freshener, dental foam, dental gel, and dental strips.

[0209] The hygiene product may be selected from joss sticks, insecticides, insect repellents, propellants, rust removers, perfumed freshening wipes, armpit pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, handkerchiefs, dishwasher deodorizer;

[0210] Cleaning compositions, such as solid surface cleaners, may be selected from perfumed acidic, alkaline and neutral cleaners, for example floor cleaners, window cleaners, dishwashing compositions for hand and machine washing, bathroom 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 polishes, disinfectants, surface disinfectants and sanitary cleaners, brake disc cleaners, pipe cleaners, descaling agents, grill and oven cleaners, algae and moss removers, mildew removers, facade cleaners.

[0211] The fabric detergent composition may be selected from liquid detergents, powder detergents, laundry pretreaters such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets.

[0212] Food means raw, cooked or processed edible substances, ice, beverages or ingredients used or intended for use, in whole or in part, for human consumption, or chewing gum, soft candy, jellies and sweets.

[0213] A dietary supplement is an edible product containing a dietary ingredient intended to further increase the nutritional value of the diet. A dietary ingredient may be one or any combination of the following: a vitamin, a mineral, a herb or other substance, an amino acid, a dietary substance used by humans to supplement the diet by increasing the total dietary intake, a concentrate, a metabolite, a component or an extract. A dietary supplement may be present in many forms, such as tablets, capsules, softgels, gelcaps, liquids or powders.

[0214] Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment or prevention of disease, as well as preparations (other than food products) intended to affect the structure or any function of the human or other animal body.

[0215] Crop protection compositions comprise compositions intended for the management of plant diseases, weeds and other pests (vertebrates and invertebrates) which damage agricultural crops and forestry.

[0216] In a preferred embodiment, the composition further comprises at least one auxiliary agent selected from the group consisting of preservatives, abrasives, anti-acne agents, anti-skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, irritation reducing agents, astringents, antiperspirants, preservatives, antistatic agents, adhesives, buffers, carrier materials, chelating agents, cell stimulants, conditioning agents, depilatories, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, anti-foaming agents, foam boosters, fungicides, gelling agents, gel formers, hair conditioners, hair fixatives, hair softeners, moisturizing agents, moisturizing substances, moisturizer substances, bleaching agents, strengthening agents, stain removers, fluorescent whitening agents, impregnation agents, soil repellents, friction reducers, lubricants, moisturizing creams, ointments, opacifiers, plasticizers, covering agents, polishing agents, shine agents, agents, polymers, powders, proteins, refatting agents, exfoliants, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin whitening agents, skin protectants, skin softeners, cooling agents, skin-cooling agents, warming agents, skin-warming agents, stabilizers, UV absorbers, 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, corrosion inhibitors, polyols, electrolytes and silicone derivatives.

[0217] For example, the method can be carried out by mixing a compound of the invention described herein with:

[0218] (i) at least one additional aroma chemical different from the compound / mixture of the present invention, or

[0219] (ii) at least one non-aroma chemical carrier, or

[0220] (iii) Both (i) and (ii).

[0221] The present invention also relates to a method for modifying the aromatic properties (e.g. fragrance profile) of an aromachemical composition, such as a perfuming composition, in particular a perfuming ready-to-use composition, wherein said method comprises incorporating into the aromachemical composition, such as a perfuming composition, in particular a perfuming ready-to-use composition, a compound of the invention as described herein.

[0222] In particular, the present invention relates to a process for preparing a fragrance composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition, comprising including a compound of the present invention as described herein in a fragrance composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition.

[0223] In one embodiment, the invention relates to a method for imparting a fragrance note reminiscent of sweet, fruity, floral, iris, powdery elements to a fragrance composition, a body care composition, a hygiene article, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition, comprising comprising a compound of the invention in a fragrance composition, a body care composition, a hygiene article, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition.

[0224] Implementation

[0225] A list of embodiments is provided below to further illustrate the present disclosure without intending to limit the present disclosure to the specific embodiments listed below.

[0226] 1. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol for imparting a fragrance impression to a composition.

[0227] 2. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0228] 3. A method for imparting a fragrance impression to a composition, comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol.

[0229] 4. A method for imparting a fragrance impression to a composition, comprising at least the step of adding a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol to the composition.

[0230] 5. The use or method according to embodiments 1-4, wherein the compound is selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E)dodec-4,11-dien-1-ol, (4Z)dodec-4,11-dien-1-ol.

[0231] 6. The use or method according to any one of the preceding embodiments, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0232] 7. The use or method according to any one of the preceding embodiments, wherein the impression is selected from aldehyde notes, fatty notes, citrus notes, clean linen notes, floral notes, marine notes, orange notes, metallic notes, waxy notes and green notes.

[0233] 8. The use or method according to any one of the preceding embodiments, wherein the compound is present in an amount of ≥ 0.01 wt.% to ≤ 70.0 wt.%, based on the total weight of the composition.

[0234] 9. A mixture comprising:

[0235] a) at least one selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and dodeca-

[0236] -4,11-diene-1-ol compounds; and

[0237] b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.

[0238] 10. A mixture according to embodiment 9, wherein dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol and mixtures of two or more thereof.

[0239] 11. The mixture according to embodiment 9, wherein the dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0240] 12. The mixture according to embodiment 9, wherein dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.

[0241] 13. The mixture according to embodiment 9, wherein 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0242] 14. The mixture according to embodiment 9, wherein 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0243] 15. A mixture according to any one of embodiments 9-14, wherein the mixture comprises: a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or

[0244] b) selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,

[0245] Any one or more compounds of (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or

[0246] c) any one or more compounds selected from (a) and (b).

[0247] 16. The mixture of any one of embodiments 9-14, wherein the mixture further comprises dodecan-1-ol.

[0248] 17. Use of the mixture according to any one of embodiments 9 to 16 as an aroma chemical.

[0249] 18. Use of the mixture according to any one of embodiments 9 to 16 for preparing an aroma chemical composition.

[0250] 19. Use of the mixture according to any one of embodiments 9 to 16 for modifying the aroma properties of an aroma chemical composition.

[0251] 20. The aroma chemical composition according to embodiments 1-8 or the mixture according to embodiments 15-16, comprising:

[0252] (i) at least one additional aroma chemical,

[0253] (ii) at least one non-aroma chemical carrier, or

[0254] (iii) A mixture of (i) and (ii).

[0255] 21. The aromachemical composition according to embodiment 20, which is a perfumed ready-to-use composition.

[0256] 22. The aroma chemical composition according to embodiment 21, wherein the perfumed ready-to-use composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0257] 23. A method for preparing a compound as defined in any one of embodiments 1-5, wherein the method comprises at least the following steps:

[0258] (i) reducing and hydrogenating dodeca-4,8,11-trienal, and optionally

[0259] (ii) Isolating the compounds.

[0260] Preferred Implementation

[0261] 1. A mixture comprising:

[0262] a) at least one selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol and dodeca-

[0263] -4,11-diene-1-ol compounds; and

[0264] b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol and 11-dodecen-1-ol.

[0265] 2. A mixture according to embodiment 1, wherein dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol and mixtures of two or more thereof.

[0266] 3. The mixture according to embodiment 1, wherein dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0267] 4. The mixture according to embodiment 1, wherein dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.

[0268] 5. The mixture according to embodiment 1, wherein 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0269] 6. The mixture according to embodiment 1, wherein 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0270] 7. The mixture according to any one of embodiments 1-6, wherein the mixture comprises:

[0271] a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or

[0272] b) selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol,

[0273] Any one or more compounds of (4E,8E)-dodec-4,8-dien-1-ol and (4Z,8Z)-dodec-4,8-dien-1-ol, or

[0274] c) any one or more compounds selected from (a) and (b).

[0275] 8. The mixture of any one of embodiments 1-7, wherein the mixture further comprises dodecan-1-ol.

[0276] 9. Use of the mixture according to any one of embodiments 1 to 8 as an aroma chemical.

[0277] 10. Use of the mixture according to any one of embodiments 1 to 8 for preparing an aroma chemical composition.

[0278] 11. Use of a mixture according to any one of embodiments 1 to 8 for modifying the fragrance properties of an aromachemical composition.

[0279] 12. An aroma chemical composition comprising a mixture according to embodiments 1 to 8, and (i) at least one additional aroma chemical,

[0280] (ii) at least one non-aroma chemical carrier, or

[0281] (iii) A mixture of (i) and (ii).

[0282] 13. The aromachemical composition according to embodiment 12, which is a perfumed ready-to-use composition.

[0283] 14. The aroma chemical composition according to embodiment 13, wherein the perfumed ready-to-use composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0284] 15. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0285] 16. A method for imparting a fragrance impression to a composition, comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol.

[0286] 17. The use or method of embodiment 15 or 16, wherein the compound is selected from (4Z,8E)-dodec-4,8-dien-1-ol, (4E,8Z)-dodec-4,8-dien-1-ol, (4E,8E)-dodec-4,8-dien-1-ol, (4Z,8Z)-dodec-4,8-dien-1-ol, (8E)-dodec-4,8-dien-1-ol, (8Z)-dodec-4,8-dien-1-ol, (4E)dodec-4,11-dien-1-ol, (4Z)dodec-4,11-dien-1-ol.

[0287] 18. The use or method according to any one of embodiments 15-17, wherein the composition is selected from the group consisting of a fragrance composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a fragrance dispenser, a food, a food supplement, a pharmaceutical composition and a crop protection composition.

[0288] 19. The use or method of any one of embodiments 15-17, wherein the impression is selected from aldehyde notes, fatty notes, citrus notes, clean linen notes, floral notes, marine notes, orange notes, metallic notes, waxy notes, and green notes.

[0289] 20. The use or method of any one of embodiments 15-17, wherein the compound is present in an amount of ≥ 0.01 wt.% to ≤ 70.0 wt.%, based on the total weight of the composition. Example

[0290] The invention is illustrated in detail by the following non-limiting examples. More particularly, the test methods described below are part of the general disclosure of the present application and are not limited to the specific working examples.

[0291] Analytical methods:

[0292] pass 13 C-NMR characterization. 13 C-NMR spectra were measured on a Bruker DPX-500 spectrometer.

[0293] GC method: Stabilwax 60m GC column combined with TOF mass spectrometry FI (field ionization).

[0294] 1. Preparation of 4,8-dodecadien-1-ol as a mixture of cis / trans isomers and a mixture of 4-dodecadien-1-ol and 8-dodecadien-1-ol

[0295] In a 3.5 L autoclave, 4,8,11-dodecatrienal (1.2 Kg, 82 mmol) was dissolved in methanol (800 g) in the presence of trimethylamine (48 g, 3 wt.%) and a Ru / Fe-based catalyst (20 g, 1.6 wt.%). The hydrogenation reaction was carried out at T = 55 ° C and 30 bar hydrogen pressure to produce 4,8-dodecadien-1-ol as a mixture of cis / trans isomers as well as 4-dodecadien-1-ol and 8-dodecadien-1-ol.

[0296] 1H NMR: product mixture: (500 MHz; CDCl3): δ [ppm] = 5.42-5.32 (m), 3.61-3.57 (m), 2.1-1.9 (m), 1.62-1.56 (m), 1.35-1.23 (m).

[0297] Depending on the hydrogenation time, different ratios of the corresponding alcohols (olefin:methylene) determined by H-NMR.

[0298] experiment Ratio of dodecenol / dodecadienol Reaction time 1a 12％ / 88％ 6 hours 1b 40％ / 60％ 8 hours 1c 66％ / 34％ 14 hours

[0299] 2. Olfactory Assessment

[0300] In order to test the odor quality and intensity of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol, and dodecan-1-ol, an odor strip test was performed.

[0301] For this purpose, absorbent paper strips are dipped into ethanolic solutions containing 1-10 wt.% of the compound to be tested. After evaporation of the solvent (approximately 30 seconds), the odor impression is evaluated olfactorily by a trained perfumer.

[0302] result:

[0303] Table 1: Odor test results

[0304]

[0305] Favorable perfume components

[0306] The compound of Example 1 was formulated into a fragrance composition according to Tables 2 and 3 and labeled as Compound A.

[0307] Table 2: Fragrance compositions 1A and 1B

[0308]

[0309]

[0310] Table 3: Fragrance compositions 2A and 2B

[0311]

[0312]

[0313] Example 1 or Example 2 in Table 1, the fragrance composition according to Table 2, Table 3, i.e., 1A, 1B, 2A, 2B may be included in the various compositions listed below;

[0314] ●Deodorant pump spray

[0315] ● Cleansing hair conditioner

[0316] Cleansing gel

[0317] Bubble bath concentrate

[0318] Hairspray

[0319] ●Self-foaming shower gel

[0320] ●Sprayable sunscreen lotion

[0321] ●Sprayable sunscreen lotion

[0322] ●Moisturizing cleansing gel

[0323] ●Two-phase oil bubble bath

[0324] ●Shampoo

[0325] Shower gel

[0326] ●Hydro-alcohol AP / deodorant pump spray

[0327] Aerosol

[0328] ●Water / alcohol AP / deodorant roll-on

[0329] ● "Out of bed" styling gel

[0330] ●Shaving foam

[0331] ●Baby shampoo for sensitive skin

[0332] ●Sensitive skin body wash

[0333] ●Shine-enhancing shampoo for sensitive scalp

[0334] ●Deodorant stick

[0335] ●Baby wipes

[0336] ●Aftershave Balm

[0337] ●Facial gel

[0338] ●Day Care Cream for Face

[0339] ● Cleansing milk

[0340] Body lotion

[0341] ●Sun protection SPF50+, sprayable lotion

[0342] ●Manual dishwashing detergent, regular

[0343] ●Manual dishwashing detergent, concentrated liquid

[0344] ● Hygiene cleaner, concentrated liquid

[0345] ●Multi-purpose cleaner

[0346] Antibacterial fabric softener

[0347] ●Detergent composition

[0348] ●Powder detergent composition

[0349] Liquid detergent composition

[0350] Those skilled in the art may be familiar with various general formulations of the above products.

[0351] Fragrance oil compositions 1A, 1B, 2A and 2B can be formulated with specific formulations such as disclosed in IP.com No.: IPCOM000258614D, titled NewAroma Chemicals, pages 6-46, Tables 1 to D13, wherein "Fragrance Composition 1A" is replaced with the same amount of Fragrance Oil Composition 1A, 1B, 2A or 2B.

Claims

1. A mixture comprising: a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, and b) selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, Any one or more compounds of (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol.

2. The mixture according to claim 1, wherein the mixture further comprises dodecan-1-ol.

3. Use of the mixture according to claim 1 or 2 as aroma chemicals.

4. Use of the mixture according to claim 1 or 2 for preparing an aromatic chemical composition.

5. Use of the mixture according to claim 1 or 2 for modifying the aroma properties of an aroma chemical composition.

6. An aromatic chemical composition comprising the mixture according to claim 1 or 2, comprising: (i) at least one additional aroma chemical, (ii) at least one non-aroma chemical carrier, or (iii) A mixture of (i) and (ii).

7. The aromachemical composition according to claim 6, which is a perfumed ready-to-use composition.

8. Aromatic chemical composition according to claim 7, wherein the perfumed ready-to-use composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

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