Esters of 5-methylhex-2-enol and their use as aroma chemicals

Abstract

The present invention relates to the use of at least one compound of formula (I) or a stereoisomer thereof, in which R is linear or branched C1-C9 alkyl, linear or branched C2-C9 alkenyl, unsubstituted or C1-C3 substituted C4-C8 cycloalkyl, or substituted or unsubstituted aryl as an aroma component. At least one compound of formula (I) can be used to impart an aroma impression to a composition reminiscent of a fruity note, a green pear note, an apple note, a juicy fruity note, a styrax note, a pineapple note, a dusty note, a watery note, or a combination of two or more notes, and to improve and / or modify the aroma of the composition. The present invention is further directed to a composition comprising at least one compound of formula (I) and (i) at least one aroma chemical different from the compound of formula (I), and / or (ii) at least one non-aroma chemical carrier. The present invention is also directed to certain compounds of formula (I) per se, and to the process for their preparation. [Case 1] TIFF2024536093000033.tif24170

Description

[Technical field]

[0001] The present disclosure relates to the use of at least one compound of formula (I) as a fragrance ingredient. At least one compound of formula (I) is used to impart a fragrance impression to a composition reminiscent of a fruity note, a green pear note, an apple note, a juicy fruity note, a styrax note, a pineapple note, a dusty note, a watery note, or a combination of two or more notes, and to improve and / or modify the fragrance of the composition. The present invention is further directed to a composition comprising at least one compound of formula (I) and (i) at least one fragrance chemical different from the compound of formula (I), or (ii) at least one non-fragrance chemical carrier, or (iii) both (i) and (ii). [Background technology]

[0002] Fragrance chemicals, especially fragrances, have attracted great attention, especially in the areas of cosmetics, cleaning and laundry compositions.

[0003] Although a large number of synthetic aroma chemicals already exist, new ingredients are constantly needed to be able to meet the many properties desired in the most diverse fields of application.These properties include, first of all, sensory properties, i.e. the compound must have favorable odor (olfactory) properties.Furthermore, aroma chemicals must also have additional positive secondary properties, such as, for example, an efficient preparation method, the possibility of providing a better sensory profile as a result of synergy with other aroma chemicals, a higher stability under certain application conditions, and / or a better and longer persistence.

[0004] Such properties are of particular interest in compositions such as, for example, care compositions, hygiene products, cleaning compositions, fabric detergent compositions, and compositions for fragrance dispensers.

[0005] Among those that are of particular interest are aroma chemicals that can provide the composition with one or more distinct sensory impressions, thereby contributing to a rich and interesting sensory profile, in particular the olfactory profile, of the composition.In this respect, attention is mainly given to aroma chemicals that can provide fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes.In addition, attention is particularly given to persistence and tenacity, so that a long-lasting odor impression is obtained not only for the composition but also for the surfaces treated with the composition.

[0006] However, the search for substances with specific and well-defined sensory properties, such as a particular odor, is very difficult, since even small changes in chemical structure can lead to large changes in sensory properties, such as odor and / or flavor. Thus, the search for new aroma chemicals is a difficult and arduous task, in most cases, without knowing whether a substance with the desired odor and / or flavor will actually be found.

[0007] The object of the invention claimed herein is to provide substances that can be used as aroma chemicals, either alone or in mixtures in compositions, and in particular strong odorous substances with a pleasant odor are required. Furthermore, they must be capable of being combined with other aroma chemicals, which allow the creation of novel and advantageous sensory profiles and can be used in compositions.

[0008] The object of the invention claimed herein is to provide novel aroma chemicals having a pleasant olfactory impression; preferably a combination of two or more of the impressions selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes.

[0009] It is a further object of the present invention to provide fragrance chemicals which are non-toxic and which should be obtained from readily available starting materials so that they can be produced quickly and economically. Summary of the Invention [Means for solving the problem]

[0010] The object of the present invention has been achieved by providing compounds of formula (I) which can be easily prepared and have a pleasant odor.

[0011] The invention claimed herein comprises at least one compound of formula (I) [ka] or its stereoisomer (In the formula, R is a linear or branched C1-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl. The present invention relates to the use of the compound of the formula (I) for imparting a fragrance impression to a composition.

[0012] A further aspect of the presently claimed invention relates to a method for imparting a fragrance impression to a composition comprising at least the step of adding to the composition at least one compound of formula (I).

[0013] Another aspect of the invention claimed herein relates to the use of at least one compound of formula (I) for modifying the fragrance characteristics of a composition.

[0014] A further aspect of the invention claimed herein relates to the use of at least one compound of formula (I) to impart a fruity note, a green pear note, an apple note, a juicy fruity note, a styrax note, a pineapple note, a dusty note, a watery note, or a combination of two or more notes to a composition.

[0015] A further aspect of the invention claimed herein relates to a method for enhancing the fragrance of a composition, said method comprising the step of mixing at least one compound of formula (I) with other ingredients, such as at least one other fragrance chemical different from the compound of formula (I) and / or at least one non-fragrance chemical carrier, to obtain a fragrance composition.

[0016] Yet another aspect of the invention claimed herein relates to a method for modifying the aroma of a composition, said method comprising the step of incorporating at least one compound of the invention claimed herein into a fragrance composition to obtain a fragrance composition having a modified aroma.

[0017] Furthermore, the compounds of formula (I) can be produced in good yield and purity by simple synthesis starting from readily available starting materials, and thus the compounds of the presently claimed invention can be produced in a facile, cost-effective manner on a large scale. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] References throughout this specification to "one embodiment" or "an embodiment" or "preferred embodiment" mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the invention claimed herein. Thus, the appearances of the phrases "in one embodiment" or "In a preferred embodiment" or "in a preferred embodiment" in various places throughout this specification do not necessarily all refer to the same embodiment, but may refer to the same embodiment. Furthermore, as will be apparent to one of ordinary skill in the art from this disclosure, features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. Furthermore, as will be appreciated by one of ordinary skill in the art, some embodiments described herein include some features but not other features included in other embodiments, and combinations of features of different embodiments are meant to form different embodiments within the scope of the subject matter. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0019] Furthermore, ranges defined throughout this specification are inclusive of end values ​​as well, i.e., a range of 1 to 10 means that both 1 and 10 are included within the range. For the avoidance of doubt, the applicant reserves the right to any equivalents available pursuant to applicable law.

[0020] The term "aroma" in the context of the present invention refers to sensory properties and includes smell and / or flavor.

[0021] The term "aroma chemical" means a substance used to obtain a sensory or organoleptic (used interchangeably herein) impression, including its use to obtain an olfactory and / or flavor impression. The term "olfactory impression" or "note" (used interchangeably herein) means an odor impression without any positive or negative judgment, whereas the term "scent impression" or "fragrance impression" or "aroma impression" (used interchangeably herein), as used herein, relates to an odor impression that is generally perceived as pleasant. Thus, "fragrance" or "aroma" means an aroma chemical that primarily induces a pleasant odor impression. Flavor means an aroma chemical that induces a taste impression.

[0022] As used herein, the term "fragrance composition" refers to a composition that induces an aroma. The term fragrance composition includes "odor composition" and / or "flavor composition." An odor composition is a composition that induces primarily an odor impression, and a flavor composition is a composition that induces primarily a taste impression.

[0023] The term "aroma profile" refers to the overall aroma impression of an aroma chemical, which is composed of the individual aroma impressions of the aroma chemicals. The term odor composition includes "fragrance composition" or "aroma composition" (used interchangeably herein) and primarily induces an odor impression that is generally perceived as pleasant.

[0024] The general expression "advantageous sensory properties" or "advantageous sensory properties" refers to the pleasantness and conciseness of the sensory impression conveyed by the aroma chemicals. "Pleasantness" and "clarity" are terms well known to those skilled in the art, such as perfumers. Pleasantness generally refers to a spontaneously generated and positively perceived pleasant sensory impression. However, "pleasantness" does not necessarily have to be synonymous with "sweetness". "Pleasantness" can also be the smell of musk or sandalwood. "Clarity" generally refers to a spontaneously generated sensory impression that is reproducibly and identically reminiscent of something specific to the same test panelist. For example, if a substance has an odor that spontaneously recalls the odor of "apple", then the odor will be distinctly "apple". If this apple odor is very pleasant, for example to recall sweet and ripe apples, then the odor is called "pleasant". However, a typically sour apple odor can also be distinct. If smelling the substance elicits both responses, in this example resulting in a pleasant, distinct apple odor, then the substance has particularly advantageous sensory properties.

[0025] When used herein in reference to a composition, method, or use of two compounds, the terms "combination," "in combination with," or "combined with" take into account the fact that the two compounds need not be used in the form of a physical mixture of the compounds, but may be used (e.g., added) separately. When compounds are used separately, they may be used (e.g., added) sequentially in any order (i.e., one after the other), or simultaneously (i.e., at essentially the same time).

[0026] The terms "boosting" or "boost" are used herein to describe the effect of enhancing and / or modifying the aroma chemicals of a fragrance composition or the aroma of a composition, respectively. The term "enhancing" includes the improvement of the pleasantness and / or clarity of the fragrance, and / or the improvement of the intensity. The term "modifying" includes the modification of the fragrance profile. The terms "pleasantness" and "clarity" are well known to those skilled in the art, such as perfumers, and have their respective meanings. Intensity can be determined by threshold determination. Although no longer necessary to define, an odor threshold is the concentration of a substance in the relevant gas space at which a representative test panelist can still perceive an odor impression.

[0027] The boosting effect is particularly desirable for perfume compositions which require applications characterized by a top note, for example in the taste area in deodorants, air fresheners or chewing gum, where the odor is delivered particularly quickly and intensively.

[0028] The terms "the present invention relates to" and "the present invention is directed to" are used interchangeably throughout the present invention.

[0029] The term "tenacity" refers to the evaporation behavior of a fragrance chemical over time. Tenacity can be determined, for example, by applying the fragrance chemical to a test strip and then olfactorily evaluating the odor impression of the test strip. For fragrance chemicals with high tenacity, the time interval during which panelists can still identify the fragrance impression is longer. The term "persistence" refers to the interaction of fragrance chemicals with a surface, for example, skin or textile, especially after subsequent treatment of the surface, for example, washing. Persistence can be determined, for example, by washing textiles with a textile detergent composition containing the fragrance chemical, followed by olfactory evaluation of the textile immediately after washing (wet textile) and evaluation of the dry textile after long-term storage.

[0030] The term "stability" describes the behavior of a fragrance chemical when in contact with oxygen, light, and / or other substances. A highly stable fragrance chemical maintains its fragrance profile, preferably over an extended period of time, in a wide variety of compositions, and under a variety of storage conditions.

[0031] In order to impart a long-lasting fragrance impression to the composition or to surfaces treated with the composition, the fragrance chemicals should preferably be highly persistent, long-lasting and stable in the composition.

[0032] The term "straight-chain C1-C9 alkyl" refers to a straight-chain saturated hydrocarbon group having 1 to 9 carbon atoms, including, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0033] The term "branched C1-C9 alkyl" refers to a branched chain saturated hydrocarbon group having 1 to 9 carbon atoms. Preferably, the branched C1-C9 alkyl is 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 4-methylhex ...hexyl, and n is an integer from 1 to 5. In one embodiment, the alkyl group is selected from 1-ethyloctyl, 5-methyloctyl, 6-methyloctyl and 7-methyloctyl, 1-ethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl and 5-ethylheptyl, 1-propylbutyl, 1-propylpentyl, 2-propylpentyl, 1-propylhexyl, or 2-propylhexyl and 3-propylhexyl.

[0034] The term "linear C2-C9 alkenyl" refers to a linear unsaturated hydrocarbon group having 2 to 9 carbon atoms. Preferably, linear C2-C9 alkenyl is ethenyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2 ... and wherein the aryl group is selected from the group consisting of non-enyl, non-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, oct-1-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl, oct-5-enyl, oct-6-enyl, oct-7-enyl, non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, and non-8-enyl.

[0035] The term branched "C2-C9 alkenyl" refers to a branched unsaturated hydrocarbon having from 2 to 9 carbon atoms.

[0036] The term "C4-C8 cycloalkyl" refers to cyclic aliphatic compounds such as cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. The cycloalkyl compounds may be substituted with C1-C3 alkyl.

[0037] The term "aryl" includes aromatic radicals such as phenyl, naphthyl, biphenyl, etc. If desired, the aryl may be optionally substituted with C1-C6 alkyl.

[0038] Unless otherwise indicated herein, "Compound (I)" as described herein refers to a compound defined by formula (I) or a salt or stereoisomer thereof.

[0039] The term "stereoisomer" is a general term used for all isomers of individual compounds that differ only in the orientation of the atoms in space, and not in the connectivity of the atoms. The term stereoisomer therefore includes mirror image isomers (enantiomers), geometric isomers (cis / trans or E / Z) isomers, and diastereoisomers. For a precise definition of the term, see G. Helmchen: "Vocabulary and Nomenclature of Organic Stereochemistry", in Houben-Weyl E21a, Stereoselective Synthesis G. Helmchen, RW Offmann, J. Mulzer, E. Schaumann (Hrsg.), 1995, 1-74. The possible isomers may exist as mixtures (i.e. racemates, cis / trans mixtures, or mixtures of diastereoisomers).

[0040] use: In one embodiment, the invention claimed herein comprises at least one compound of formula (I): [ka] or its stereoisomer (In the formula, R is a linear or branched C1-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl. The present invention relates to the use of the compound of the formula (I) for imparting a fragrance impression to a composition.

[0041] In one embodiment, R is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylhexyl, 5-methylhexyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methyl 1-ethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, and 5-ethylheptyl, 1-propylbutyl, 1-propylpentyl, 2-propylpentyl, 1-propylhexyl, 2-propylhexyl, 3-propylhexyl, ethenyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept ...2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-en In some embodiments, the aryl group is selected from the group consisting of oct-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, oct-1-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl, oct-5-enyl, oct-6-enyl, oct-7-enyl, non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, or non-8-enyl, cyclohexyl, methylcyclohexyl, phenyl, and 4-methylphenyl.

[0042] Preferably, R is methyl, ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexyl, phenyl, or 4-methylphenyl. More preferably, R is methyl.

[0043] In one embodiment, the compound of formula (I) is a single stereoisomer, the cis isomer Ia [ka] and Trans isomer Ib [ka] in a ratio ranging from 0.01 to 99.99 to 99.99 to 0.01, In the formula, R is methyl.

[0044] In one embodiment, the compound of formula (I) is a compound of formula (Ib').

[0045] In one embodiment, a compound of formula (Ib') [ka] is a compound of formula (IIa) [ka] in the range of 1.0% by weight to 0.01% by weight, preferably in the range of 0.8% by weight to 0.01% by weight, and more preferably in the range of 0.6% by weight to 0.01% by weight.

[0046] Those skilled in the art can isolate the compounds of formula (Ia) and (Ib).These compounds can be used to prepare any desired ratio of mixtures of the compounds of formula (Ia) and formula (Ib).This ratio can be determined by those skilled in the art depending on the end use of the combination in any suitable composition.

[0047] A preferred embodiment of the invention claimed herein is directed to the use of at least one compound of formula (I) as an aroma chemical to impart an aroma impression selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes, or a combination of two or more notes.

[0048] In a further embodiment, the invention claimed herein is directed to the use of at least one compound of formula (I) for enhancing the fragrance of a composition.

[0049] In one embodiment of the presently claimed invention, at least one compound of formula (I) is used as a component of a fragrance or fragrance composition.

[0050] In particular, at least one compound of formula (I) is used to impart to the composition a note selected from a fruity note, a green pear note, an apple note, a juicy fruity note, a styrax note, a pineapple note, a dusty note, a watery note, or a combination of two or more notes.

[0051] Preferably, the compounds of formula (Ib') are used to impart to the composition a combination of two or more impressions selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes.

[0052] The presence of the compound of formula (IIa) does not affect the odor impression of the compound of formula (Ib').

[0053] Suitable compositions are, for example, compositions used in personal care, home care, industrial applications, but also in other applications such as pharmaceutical compositions or crop protection compositions.

[0054] Preferably, the compounds of formula (I) according to the presently claimed invention are used in a composition selected from a perfume composition, a body care composition (including cosmetic compositions and oral and dental hygiene products), a hygiene product, a cleaning composition (including dishwashing compositions), a textile detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition, or a crop protection composition.

[0055] The compositions are described in more detail in the following paragraphs.

[0056] Compound: One embodiment of the present invention is a compound of formula (I) [ka] or its stereoisomer (In the formula, R is a linear or branched C2-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl.

[0057] Another embodiment of the present invention is a compound of formula (Ib) [ka] , (in the formula, R is a linear or branched C2-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl.

[0058] In one embodiment of the invention, R is ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-methylheptyl, 2-methylheptyl, 3-methylhept ... 1-ethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, aryl, 5-ethylheptyl, 1-propylbutyl, 1-propylpentyl, 2-propylpentyl, 1-propylhexyl, 2-propylhexyl and 3-propylhexyl, ethenyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hex ... hex-2-enyl, hex-2-enyl, hex-3-enyl, hex-4 and wherein the aryl group is selected from aryl, aryl-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, oct-1-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl, oct-5-enyl, oct-6-enyl, oct-7-enyl, non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, non-8-enyl, cyclohexyl, methylcyclohexyl, phenyl, or 4-methylphenyl.

[0059] Preferably, R is ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexylphenyl, or 4-methylphenyl.

[0060] Preferably, R is ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, phenyl, or 4-methylphenyl.

[0061] Composition: In one embodiment, the invention claimed herein comprises at least one compound of formula (I): (i) at least one aroma chemical (X) different from the compound of formula (I), or (ii) at least one non-aromatic chemical carrier; or (iii) A composition comprising both (i) and (ii).

[0062] Preferably, in this embodiment, the composition comprises the compounds of formula (I) in a total amount ranging from 0.01% to 70.0% by weight, based on the total weight of the composition.

[0063] Preferably, the composition is a fragrance composition, more preferably a fragrance composition.

[0064] In one embodiment, the compound of formula (I) is a compound of formula (Ib) and the composition is made as set forth in the preceding paragraph.

[0065] In one embodiment, the compound of formula (I) is a compound of formula (Ib') and the composition is made as set forth in the preceding paragraph.

[0066] The aroma chemical is different from the compound of formula (I).

[0067] In one preferred embodiment, the composition comprises at least one fragrance chemical different from the compound of formula (I). The fragrance chemical different from the compound of formula (I) is also referred to as fragrance chemical (X).

[0068] Due to their physical properties, the compounds of formula (I) can be successfully combined with different aroma chemicals and other conventional ingredients in fragrance compositions, especially perfume compositions.This allows, for example, the creation of aroma compositions (preferably perfume compositions) with novel and advantageous sensory profiles.In particular, as already explained above, the compounds can provide a boosting effect to other aroma chemicals (such as perfumes).

[0069] The aroma chemicals (X) are preferably selected from: Geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, cyclohexyl acetate, alpha-ionone, n-alpha-methyl ionone, alpha-isomethyl ionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-carboxaldehyde, alpha-amylcinnamaldehyde, ethylene brassylate, (E)- and / or (Z)-3-methylcyclopentadeca-5-enone, 15-pentadeca-11-enolide and / or 15-pentadeca-12-enolide, 15-cyclopentadeca-nolide, 1-(5,6,7, 8-Tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-Dimethyl-5-hepten-1-al, borneol, 3(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)-propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octyl tetrahydronaphthalene-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, or 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.

[0070] In a preferred embodiment, the at least one aroma chemical (X) 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, or methyl benzoate.

[0071] In another preferred embodiment, the at least one aroma chemical (X) is selected from ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol), or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0072] Further fragrance chemicals with which the compounds of formula (I) can be combined to obtain compositions according to the invention claimed herein can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published or H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 4th Ed., Wiley- VCH, Weinheim 2016. In particular, the following can be mentioned: Extracts from natural sources, such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, e.g. Ambergris Tincture, Amyris Oil, Angelica Seed Oil, Angelica Root Oil, Anise Oil, Valerian Oil, Basil Oil, Tree Moss Absolute, Bay Oil, Wormwood Oil, Benzoin Resin, Bergamot Oil, Beeswax Absolute, Birch Tar Oil, Bitter Almond Oil, Savory Oil, Butu Leaf Oil, Cabreva Oil, Cade Oil, Calmus Oil, Camphor Oil, Cananga Oil, Cardamom Oil, Cascarilla Oil, Cassia Oil, Cassia Absolute, Castorium Absolute, Cedar Leaf Oil, Cedarwood Oil, Cistus Oil, Citronella Oil, Lemon Oil, Copaiba Balsam, Copaiba Balsam Oil, Coriander Oil, Costus Root Oil, Cumin Oil, Cypress Oil, Davana Oil, Dill Weed Oil, Dill Seed Oil, Eau de brouts absolute, oakmoss absolute, elemi oil, tarragon oil, eucalyptus citriodora oil, eucalyptus oil, fennel oil, pine needle oil, galbanum oil, galbanum resin, geranium oil, grapefruit oil, guaiacwood oil, gurjan balsam, gurjan balsam oil, helichrysum absolute, helichrysum oil, ginger oil, iris root absolute, iris root oil, jasmine absolute, chamus oil, chamomile oil blue, roman chamomile oil, carrot seed oil, cascarilla oil, pine needle oil, spearmint oil, caraway oil, labdanum Oil, Labdanum Absolute, Labdanum Resin, Lavandin Absolute, Lavandin Oil, Lavender Absolute, Lavender Oil, Lemongrass Oil, Lovage Oil, Distilled Lime Oil, Pressed Lime Oil, Linalool Oil, Litsea Cucumber Oil, Bay Leaf Oil, Mace Oil, Marjoram Oil, Mandarin Oil, Massoia Bark Oil, Mimosa Absolute, Musk Seed Oil, Mus Tinker, Clary Sage Oil, Nutmeg Oil, Myrrh Absolute, Myrrh Oil, Myrrh Oil, Myrtle Oil, Clove Leaf Oil, Clove Flower Oil, Neroli Oil, Olibanum Absolute, Olibanum Oil, Opopanax Oil,Orange Blossom Absolute, Orange Oil, Origanum Oil, Palmarosa Oil, Patchouli Oil, Parilla Oil, Balsam of Peru Oil, Parsley Leaf Oil, Parsley Seed Oil, Petitgrain Oil, Peppermint Oil, Pepper Oil, Pimento Oil, Pine Oil, Pennyroyal Oil, Rose Absolute, Rosewood Oil, Rose Oil, Rosemary Oil, Dalmatian Sage Oil, Spanish Sage Oil, Sandalwood Oil, Celery Seed Oil, Spike Lavender Oil, Sta - anise oil, styrax oil, tagetes oil, fir needle oil, tea tree oil, turpentine oil, thyme oil, tolu balsam, tonka absolute, tuberose absolute, vanilla extract, violet leaf absolute, verbena oil, vetiver oil, juniper berry oil, wine wreath oil, absinthe oil, wintergreen oil, hyssop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil and fractions or components isolated therefrom; Individual fragrances from the group of hydrocarbons, such as 3-carene, α-pinene, β-pinene, α-terpinene, γ-terpinene, p-cymene, bisabolene, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, (E,Z)-1,3,5-undecatriene, styrene, diphenylmethane, etc. Aliphatic alcohols, such as hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, (E)-2-hexenol, (E)- and (Z)-3-hexenol, 1-octen-3-ol, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc. Aliphatic aldehydes and their acetals, such as hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, 2-methyloctanal, 2-methylnonanal, (E)-2-hexenal, (Z)-4-heptenal, 2,6-dimethyl-5-heptenal, 10-undecenal, (E)-4-decenal, 2-dodecenal, 2,6,10-trimethyl-9-undecenal, 2,6,10-trimethyl-5,9-undecadienal; aliphatic ketones and their oximes, such as 2-heptanone, 2-octanone, 3-octanone, 2-nonanone, 5-methyl-3-heptanone, 5-methyl-3-heptanone oxime, 2,4,4,7-tetramethyl-6-octen-3-one, 6-methyl-5-hepten-2-one, etc. Sulfur-containing aliphatic compounds, such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, 1-menthene-8-thiol, etc. Aliphatic nitriles, such as 2-nonenenitrile, 2-undecenenitrile, 2-tridecenenitrile, 3,12-tridecadienonitrile, 3,7-dimethyl-2,6-octadienenitrile, 3,7-dimethyl-6-octenenitrile, etc. Esters of aliphatic carboxylic acids, for example (E) and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, hexyl acetate, 3,5,5-trimethylhexyl acetate, 3-methyl-2-butenyl acetate, (E)-2-hexenyl acetate, (E) and (Z)-3-hexenyl acetate, octyl acetate, 3-octyl acetate, 1-octen-3-yl acetate, ethyl butyrate, butyl butyrate, isoamyl butyrate, hexyl butyrate, (E) and (Z)-3-hexenyl isobutyrate, hexyl crotonate, ethyl isovalerate, ethyl 2-methylpentanoate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, allyl heptanoate, ethyl octanoate, ethyl (E,Z)-2,4-decadienoate, methyl 2-octinate, methyl 2-noninate, allyl 2-isoamyloxyacetate, methyl-3,7-dimethyl-2,6-octadienoate, 4-methyl-2-pentyl crotonate, etc. Acyclic terpene alcohols, such as geraniol, nerol, linalool, lavandulol, nerolidol, farnesol, tetrahydrolinalool, 2,6-dimethyl-7-octen-2-ol, 2,6-dimethyloctan-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 2,6-dimethyl-5,7-octadien-2-ol, 2,6-dimethyl-3,5-octadien- 2-ol, 3,7-dimethyl-4,6-octadien-3-ol, 3,7-dimethyl-1,5,7-octatrien-3-ol, 2,6-dimethyl-2,5,7-octatrien-1-ol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates, Acyclic terpene aldehydes and ketones, such as geranial, neral, citronellal, 7-hydroxy-3,7-dimethyloctanal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9 undecenal, geranyl acetone, and the dimethyl and diethyl acetals of geranial, neral, and 7-hydroxy-3,7-dimethyloctanal; cyclic terpene alcohols, such as menthol, isopulegol, α-tert-butyl ether, methyl ... Pineol, terpin-4-ol, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambrinol, vetiverol, guajole, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates, etc. Cyclic terpene aldehydes and ketones, such as menthone, isomenthone, 8-mercaptomenthan-3-one, carvone, camphor, fenchone, α-ionone, β-ionone, α-n-methylionone, β-n-methylionone, α-isomethylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, γ-damascone, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl) -2-Buten-1-one, 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, nootkatone, dihydronootkatone, 4,6,8-megastigmatrien-3-one, α-sinensal, β-sinensal, acetylated cedarwood oil (methyl cedryl ketone), etc. Cyclic alcohols, such as 4-tert-butylcyclohexanol, 3,3,5-trimethylcyclohexanol, 3-isocamphylcyclohexanol, 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, etc. Alicyclic alcohols, such as α-3,3-trimethylcyclohexylmethanol, 1(4-isopropylcyclohexyl)ethanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl)pentan-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, etc. Cyclic and alicyclic ethers, such as cineole, cedryl methyl ether, cyclododecyl methyl ether, 1,1-dimethoxycyclo-dodecane, (ethoxymethoxy)cyclo-dodecane, α-cedrene epoxide, 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 3a-ethyl-6,6,9a-trimethyldodecahydro-naphtho[2,1-b]furan, 1,5,9-trimethyl-13-oxabicyclo-[10.1.0]trideca-4,8-diene, rose oxide, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane, etc. Cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone, 2,2,5-trimethyl-5-pentylcyclo-pentanone, 2-heptylcyclopentanone, 2-pentylcyclo-pentanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one, 3-methyl-2-pentyl-2-cyclopenten-1-one, 3-methyl-4-cyclopentadecenone, 3-methyl-5-cyclopentadecenone, 3- Methylcyclopentadecanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 4-tert-pentylcyclohexanone, 5-cyclohexadecen-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 8-cyclohexadecen-1-one, 7-cyclohexadecen-1-one, (7 / 8)-cyclohexadecen-1-one, 9-cycloheptadecen-1-one, cyclopentadecanone, cyclohexadecanone, etc. Alicyclic aldehydes, such as 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde, etc. Alicyclic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one, 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone, methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone, tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl)ketone, etc. Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate, 4-tert-butylcyclohexyl acetate, 2-tert-pentylcyclohexyl acetate, 4-tert-pentylcyclohexyl acetate, 3,3,5-trimethylcyclohexyl acetate, decahydro-2-naphthyl acetate, 2-cyclopentylcyclopentyl crotonate, 3-pentyltetrahydro-2H-pyran-4-yl acetate. decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate, 4,7-methanooctahydro-5 or 6-indenyl acetate, etc. Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate, Esters of alicyclic carboxylic acids, such as allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis- and trans-methyl dihydrojasmonate, cis- and trans-methyl jasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6,6 dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, ethyl 2-methyl-1,3-dioxolane-2-acetate, and the like; Aromatic aliphatic alcohols, such as benzyl alcohol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethyl alcohol, 1,1-dimethyl-3-phenylpropanol, 1-ethyl-1-methyl-3-phenylpropanol, 2-methyl-5-phenylpentanol, 3-methyl-5-phenylpentanol, 3-phenyl-2-propen-1-ol, 4-methoxy-benzyl alcohol, 1-(4-isopropylphenyl)ethanol, etc. Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate, benzyl propionate, benzyl isobutyrate, benzyl isovalerate, 2-phenylethyl acetate, 2-phenylethyl propionate, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, 1-phenylethyl acetate, α-trichloromethylbenzyl acetate, α,α-dimethylphenylethyl acetate, α,α-dimethylphenylethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, 4-methoxybenzyl acetate, etc. Aromatic aliphatic ethers, such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine, etc. Aromatic and araliphatic aldehydes, such as benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, hydratropaldehyde, 4-methylbenzaldehyde, 4-methylphenylacetaldehyde, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 2-methyl-3-(4-isopropylphenyl)propanal, 2-methyl-3-(4-tert-butylphenyl)propanal, 2-methyl-3-(4-isobutylphenyl)propanal, 3-(4-tert-butylphenyl)propanal; cinnamaldehyde, α-butylcinnamaldehyde, α-amylcinnamaldehyde, α-hexylcinnamaldehyde, 3-methyl-5-phenylpentanal, 4-methoxybenzaldehyde, 4-hydroxy-3-methoxy-benzaldehyde, 4-hydroxy-3-ethoxybenzaldehyde, 3,4-methylenedioxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 2-methyl-3-(4-methoxyphenyl)propanal, 2-methyl-3-(4-methylenedioxyphenyl)propanal, etc. Aromatic and araliphatic ketones, such as acetophenone, 4-methylacetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthalenyl)-ethanone, 2-benzofuranyl-ethanone, (3-methyl-2-benzofuranyl)ethanone, benzophenone 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone, 6-tert-butyl-1,1 dimethyl-4 indanyl methyl ketone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5 indenyl]ethanone, 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2'-acetonaphthone, etc. Aromatic and aliphatic carboxylic acids and their esters, such as benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenyl acetate, ethyl phenyl acetate, geranyl phenyl acetate, phenylethyl phenyl acetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, cinnamyl cinnamate, allyl phenoxy acetate, methyl salicylate, isoamyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate, etc. Nitrogen-containing aromatic compounds, such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene, 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone, cinnamonitrile, 3-methyl-5-phenyl-2-pentenonitrile, 3-methyl-5-phenylpentanonitrile, methyl anthranilate, methyl-N-methyl anthranilate, 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or the Schiff base of methyl anthranilate with 2,4-dimethyl-3-cyclohexenecarbaldehyde, 6-isopropylquinoline, 6-isobutylquinoline, 6-sec-butylquinoline, 2-(3-phenylpropyl)pyridine, indole, skatole, 2-methoxy-3-isopropyl-pyrazine, 2-isobutyl-3-methoxypyrazine, etc. Phenols, phenyl ethers and phenyl esters, such as estragole, anethole, eugenol, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, β-naphthyl methyl ether, β-naphthyl ethyl ether, β-naphthyl isobutyl ether, 1,4-dimethoxybenzene, eugenyl acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, p-cresyl phenyl acetate, etc. Heterocyclic compounds, such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one, 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one, 3-hydroxy-2-methyl-4H-pyran-4-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, etc. Lactones, for example 1,4-octanolide, 3-methyl-1,4-octanolide, 1,4-nonanolide, 1,4-decanolide, 8-decen-1,4-olide, 1,4-undecanolide, 1,4-dodecanolide, 1,5-decanolide, 1,5-dodecanolide, 4-methyl-1,4-decanolide, 1,15-pentadecanolide, cis and trans-11-pentadecanolide, cis and trans-1 2-Pentadecen-1,15-olide, 1,16-hexadecanolide, 9-hexadecen-1,16-olide, 10-oxa-1,16-hexadecanolide, 11-oxa-1,16-hexadecanolide, 12-oxa-1,16-hexadecanolide, ethylene 1,12-dodecanedioate, ethylene 1,13-tridecanedioate, coumarin, 2,3-dihydrocoumarin, octahydrocoumarin, and the like.

[0073] The fragrance chemicals (X) used in the compositions are obtained from known commercial sources and are sourced from Germany.

[0074] In a preferred embodiment, the composition comprises at least one compound of formula (I) and at least one fragrance chemical (X).

[0075] Non-fragrance Chemical Carriers: The non-fragrance chemical carriers in the compositions of the present invention are preferably selected from surfactants, oil components, antioxidants, deodorant actives, and solvents.

[0076] Preferably, the at least one non-aroma chemical carrier is a compound, mixture of compounds, or other additive that has no sensory properties or no noticeable sensory properties. When included in the composition, the non-aroma chemical carrier may serve to dilute and / or immobilize the compound of formula (I) and, optionally, at least one aroma chemical (X) as defined above.

[0077] The non-fragrance chemical carrier in the compositions of the present invention is preferably selected from a surfactant, an oil component, a solvent, or any mixture of two or more of the foregoing.

[0078] solvent In the context of the invention claimed herein, a "solvent" is one which has no fragrance of its own and serves to dilute the compound of formula (I) used according to the invention.

[0079] The amount of solvent is adjusted depending on the composition and represents a routine task for those skilled in the art.

[0080] Preferably, the solvent is present in the composition in a total amount of from 0.01% to 99.0% by weight, more preferably in a total amount of from 0.05% to 95.0% by weight, even more preferably in a total amount of from 0.1% to 80.0% by weight, most preferably in a total amount of from 0.1% to 70.0% by weight, especially from 0.1% to 60.0% by weight, based on the total weight of the composition.

[0081] In a preferred embodiment, the composition comprises 0.05% to 10% by weight, more preferably 0.1% to 5% by weight, even more preferably 0.2% to 3% by weight of total solvents based on the total weight of the composition. In yet another preferred embodiment of the present invention, the composition comprises 20% to 70% by weight, more preferably 25% to 50% by weight of total solvents based on the total weight of the composition.

[0082] Preferred solvents are selected from ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2 butylene glycol, dipropylene glycol, triethyl citrate, isopropyl myristate, or any mixture of two or more of the foregoing.

[0083] In a preferred embodiment, the composition comprises a compound of formula (I), at least one solvent, and optionally at least one fragrance chemical (X).

[0084] Oil ingredients Preferably, the total oil component is present in an amount from 0.1 to 80 wt.%, more preferably from 0.5 to 70 wt.%, even more preferably from 1 to 60 wt.%, even more preferably from 1 to 50 wt.%, particularly from 1 to 40 wt.%, more particularly from 5 to 25 wt.%, especially from 5 to 15 wt.%, based on the total weight of the composition.

[0085] Preferably, the oil component is Guerbet alcohols based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, and other further esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate. In one embodiment, the oleyl ester is selected from the group consisting of oleyl ester, isostearyl ...Also included are esters of C18 to C38 alkyl-hydroxycarboxylic acids with linear or branched C6 to C22 fatty alcohols, more particularly dioctyl malate, esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol), triglycerides based on C6 to C10 fatty acids, liquid mono-, di- and triglyceride mixtures based on C6 to C18 fatty acids, esters of C6 to C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alkanols, esters of benzoic acid, ... Suitable are choline, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates, such as, for example, dicaprylyl carbonate (Cetiol® CC), Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, esters of benzoic acid with linear and / or branched C6-C22 alcohols (for example, Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons, or mixtures thereof.

[0086] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one oil component, and optionally at least one fragrance chemical (X).

[0087] Antioxidants It will be understood that an antioxidant is one capable of inhibiting or preventing undesirable changes in the composition to be protected caused by oxygen effects and other oxidation processes. The effect of antioxidants consists in acting, in most cases, as free radical scavengers against the free radicals generated during autoxidation.

[0088] In a preferred embodiment, the antioxidant is selected from: Amino acids (e.g., glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives, Imidazoles (e.g. urocanic acid) and their derivatives, Peptides such as D,L-carnosine, D-carnosine, L-carnosine (=β-alanyl-L-histidine) and their derivatives, Carotenoids, carotenes (e.g. α-carotene, β-carotene, lycopene, lutein) or derivatives thereof, Chlorogenic acid and its derivatives, Lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters) and their salts, Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts), Sulfoximine compounds (e.g. buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa-, and heptathionine sulfoximine), (Metal) chelating agents (e.g. alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), Humic acid, bile acids, bile extract, bilirubin, biliverdin, boldine (= alkaloids derived from the plant Peumus boldus), boldo extract, EDTA, EGTA and their derivatives, Unsaturated fatty acids and their derivatives (e.g., gamma-linolenic acid, linoleic acid, oleic acid), Folic acid and its derivatives, Ubiquinone and ubiquinol and their derivatives, Vitamin C and derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), Tocopherol and derivatives (e.g. vitamin E acetate), Vitamin A and derivatives (e.g. vitamin A palmitate), Benzoin gum's coniferyl benzoate, rutin acid and its derivatives, α-glycosyl rutin, ferulic acid, furfurylidene glucitol, Butylated hydroxytoluene (BHT), Butylated hydroxyanisole (BHA), Nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, Superoxide dismutase, Zinc and its derivatives (e.g. ZnO, ZnSO4), Selenium and its derivatives (e.g. selenomethionine), Stilbene and its derivatives (e.g. stilbene oxide, trans-stilbene oxide), or a mixture of two or more of the foregoing.

[0089] In a preferred embodiment, the antioxidant is selected from pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ascorbyl palmitate, tocopherol, or a mixture of two or more of the foregoing.

[0090] Preferably, the compositions according to the invention claimed herein comprise the antioxidant in a total amount of 0.001 to 25 wt.%, preferably 0.005 to 10 wt.%, more preferably 0.01 to 8 wt.%, even more preferably 0.025 to 7 wt.%, and even more preferably 0.05 to 5 wt.%, based on the total weight of the composition.

[0091] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one antioxidant, and optionally at least one fragrance chemical (X).

[0092] Deodorizing agent Deodorant compositions (deodorants and antiperspirants) neutralize, mask or eliminate body odor, which is caused by the action of skin bacteria on apocrine sweat, resulting in the formation of unpleasant-smelling decomposition products.

[0093] Preferably, the deodorant active is selected from an antiperspirant, an esterase inhibitor, an antimicrobial agent, or a mixture of two or more of the foregoing.

[0094] Suitable antiperspirants are selected from aluminum, zirconium or zinc salts. Examples are aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complexes, for example with 1,2-propylene glycol, aluminum hydroxyalantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and their complexes, for example with amino acids, for example with glycine. Aluminum chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate or their complexes are preferably used.

[0095] Preferably, the antiperspirant is selected from aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxyalantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, or a mixture of two or more of the foregoing.

[0096] When sweat is present in the armpit area, extracellular enzymes esterases, mainly proteases and / or lipases, are formed by bacteria and break down the esters present in sweat, releasing odor in the process.Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate.Esterase inhibitors inhibit enzyme activity, thereby reducing odor generation.The cleavage of citrate esters probably releases free acids, lowering the pH value of the skin to such an extent that enzymes are inactivated by acylation. Other esterase inhibitors are, for example, sterol sulfates or phosphates such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, for example, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and their esters, for example, citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, zinc glycinate, and mixtures of two or more of the foregoing.

[0097] Preferably, the esterase inhibitor is selected from trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester, zinc glycinate, or a mixture of two or more of the foregoing.

[0098] Preferably, the compositions according to the invention claimed herein contain the esterase inhibitor in a total amount in the range of 0.01 to 20% by weight, preferably 0.1 to 10% by weight, more particularly 0.5 to 5% by weight, based on the total weight of the composition.

[0099] The term "antimicrobial agent" as used herein includes substances that have bactericidal and / or bacteriostatic properties.Typically, these substances include, for example, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-4-hydroxybenzoic acid, ... -propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), and salicylic acid-N-alkylamides, such as salicylic acid-n-octylamide or salicylic acid-n-decylamide, act against gram-positive bacteria.

[0100] Preferably, the antibacterial agent is chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides, or a mixture of two or more of the foregoing.

[0101] Preferably, the compositions according to the invention claimed herein contain the antimicrobial agent in a total amount in the range of 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the total weight of the composition.

[0102] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one deodorant active, and optionally at least one fragrance chemical (X).

[0103] Surfactants Preferably, the surfactant is selected from anionic, nonionic, cationic, amphoteric, zwitterionic surfactants, or a mixture of two or more of the foregoing. More preferably, the surfactant is an anionic surfactant.

[0104] Preferably, the composition according to the invention comprises surfactants in a total amount of 0 to 40% by weight, more preferably 0 to 20% by weight, more preferably 0.1 to 15% by weight, especially 0.1 to 10% by weight, based on the total weight of the composition.

[0105] Preferred nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alkyl(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkylglucamides, protein hydrolysates (especially wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. When the nonionic surfactants contain polyglycol ether chains, they can have a conventional homolog distribution, but preferably have a narrow range homolog distribution.

[0106] Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one COO(-) or SO3(-) group in the molecule.

[0107] Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethylhydroxyethylcarboxymethylglycinate. Particularly preferred are the fatty acid amide derivatives known under the CTFA name of cocamidopropyl betaine.

[0108] Amphoteric surfactants are also particularly suitable as cosurfactants. Amphoteric surfactants are surface-active compounds that contain at least one free amino group and at least one -COOH or SO3H group in the molecule in addition to a C8-C18 alkyl or acyl group and can form an intramolecular salt. Examples of suitable amphoteric surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl amino butyric acids, N-alkyl imino dipropionic acids, N-hydroxyethyl-N-alkyl amidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkyl amino propionic acids and alkyl amino acetic acids, with the alkyl group having about 8 to 18 carbon atoms. Particularly preferred amphoteric surfactants are N-coco alkyl amino propionates, coco acyl amino ethyl amino propionates and acyl sarcosines.

[0109] Anionic surfactants are characterized by a water-soluble anionic group, such as a carboxylate, sulfate, sulfonate or phosphate group, and a lipophilic group. Dermatologically safe anionic surfactants are known to many practitioners from the relevant textbooks and are commercially available. They are in particular alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts, alkyl ether sulfates containing linear C12-C18 alkyl or acyl groups, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, as well as sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.

[0110] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more particularly chlorides and bromides such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride and trialkylmethylammonium chloride, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. In addition, easily biodegradable quaternary ester compounds may be used as cationic surfactants, such as dialkylammonium methosulfate and methylhydroxyalkyldialkyloxyalkylammonium methosulfate, which are commercially available under the name Stepantexe, and the corresponding products of the Dehyquart® series. "Ester quats" are generally understood to be quaternized fatty acid triethanolamine ester salts. They can impart a certain softness to the composition. They are known substances that are prepared by the relevant methods of organic chemistry. Other cationic surfactants suitable for use according to the invention are quaternized protein hydrolysates.

[0111] Due to the characteristic sensory properties of the compounds of formula (I) and their substantivity, tenacity and stability, the compounds of formula (I) can be used in particular to impart an odor, preferably a perfume impression, to surfactant-containing compositions, such as detergents, especially laundry care products and multi-purpose detergents.Preferably, they can be used to impart a long-lasting note to the surfactant-containing composition, selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes and watery notes.

[0112] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one surfactant, and optionally at least one fragrance chemical (X).

[0113] Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, dietary supplements, pharmaceutical compositions and crop protection compositions.

[0114] The perfume compositions may be selected from fine fragrances, air fresheners in liquid, gel or applied to a solid carrier, aerosol sprays, scented cleansers, perfumed candles and oils such as lamp oils or massage oils.

[0115] Examples of fine fragrances are perfume extracts, Eau de Parfum, Eau de Toilette, Eau de Cologne, Eau de Solide and Extrait Parfum.

[0116] Body care compositions include cosmetic compositions and oral and dental hygiene products, including aftershave products, preshave products, splash colognes, bar and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions, such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, aftersun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, suntan creams and lotions, etc., hair care products, such as hairsprays, hair gel ... hair shaping compositions such as hair gels, setting hair lotions, hair conditioners, hair shampoos, permanent and semi-permanent hair colorants, cold wave and hair smoothing compositions, hair tonics, hair creams and hair lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, decorative cosmetic products such as eyeliners, eye shadows, nail polishes, make-up products, lipsticks and mascaras, and oral and dental hygiene products such as toothpastes, dental floss, mouthwashes, breath fresheners, dental foams, dental gels, and dental strips.

[0117] The hygiene products may be selected from incense sticks, insecticides, repellents, sprays, rust removers, scented freshening wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, pocket tissues, dishwashers and deodorants.

[0118] Cleaning compositions such as cleaners for solid surfaces may be selected from scented acidic, alkaline and neutral cleaners, e.g. floor cleaners, window cleaners, dishwashing compositions for both hand and machine washing, bathroom and sanitary cleaners, scouring milks, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polishes, floor waxes, shoe creams, disinfectants, surface disinfectants and sanitary cleaners, brake cleaners, pipe cleaners, limescale removers, grill and oven cleaners, algae and moss removers, mould removers, exterior wall cleaners.

[0119] The textile detergent composition may be selected from liquid detergents, powder detergents, laundry pre-treatments such as bleaches, soaking agents and stain removers, fabric softeners, laundry soaps, laundry tablets.

[0120] Food means any raw, cooked, or processed edible substance, ice, beverage, or composition used or intended to be used in whole or in part for human consumption, or chewing gum, gummies, jellies, and confectioneries.

[0121] A dietary supplement is a product intended to be ingested that contains dietary ingredients that are intended to add additional nutritional value to the diet. The dietary ingredients can be one or any combination of the following substances: vitamins, minerals, herbs or other botanicals, amino acids, dietary substances used by humans to supplement the diet by increasing total dietary intake, concentrates, metabolites, constructs or extracts. Dietary supplements can be found in many forms, such as tablets, capsules, softgels, gelcaps, liquids, or powders.

[0122] Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease, as well as articles (other than food) intended to affect the structure or any function of the body of humans or other animals.

[0123] Crop protection compositions include compositions intended for the management of plant diseases, weeds and other pests (both vertebrate and invertebrate) which damage agricultural crops and forests.

[0124] Preferably, the composition according to the invention is selected from the group consisting of antiseptics, abrasives, anti-acne agents, agents for combating skin aging, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, inflammation suppressing agents, irritation relieving agents, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffering agents, carrier materials, chelating agents, cell stimulants, care agents, depilatories, emulsifiers, enzymes, essential oils, fibres, film-forming agents, fixatives, foaming agents, foam stabilising agents, foam inhibitors, foam accelerators, bactericides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair smoothing agents, moisture donating agents, moisturising agents, humectants, bleaching agents, strengthening agents, stain removers, optical brighteners, impregnating agents, antifouling agents, friction reducing agents, lubricants, moisturising creams, ointments, milk The composition may further comprise at least one auxiliary selected from whitening agents, plasticizers, coating agents, polishing agents, glossing agents, polymers, powders, proteins, refatting agents, exfoliants, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin whitening agents, skin protection agents, skin emollients, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbers, UV filters, 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, liquefying agents, dyes, color protection agents, pigments, corrosion inhibitors, polyols, electrolytes, and silicone derivatives.

[0125] Composition preparations and methods for imparting a fragrance impression to a composition. One embodiment of the present invention comprises: (i) at least one aroma chemical (X) other than a compound according to the invention, or (ii) at least one non-aromatic chemical carrier; or The present invention is directed to a method for preparing a composition of at least one compound of formula (I), comprising both (i) and (ii).

[0126] The present invention is also directed to a method for enhancing the fragrance impression of a composition, comprising incorporating at least one compound of formula (I) in the composition.

[0127] In particular, the present invention is directed to a method for preparing a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising including at least one compound of formula (I) in the perfume composition, the body care composition, the hygiene product, the cleaning composition, the textile detergent composition, the composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0128] In one embodiment, the present invention is directed to a method for imparting notes reminiscent of sweet, technical, tobacco, balsamic, herbal, fruity, woody elements to a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising including at least one compound of formula (I) in the perfume composition, the body care composition, the hygiene product, the cleaning composition, the textile detergent composition, the fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0129] amount Generally, the total amount of the compound of formula (I) in the compositions, methods and uses according to the present invention is typically adapted to the specific intended use or intended application and can therefore vary over a wide range.As a rule, the usual standard commercial amounts of aroma chemicals, preferably fragrances, are used.

[0130] Preferably, the composition according to the present invention comprises the compound of formula (I) in a total amount of 0.001 to 99.9% by weight, based on the total weight of the composition.

[0131] In particular, the composition comprises the compound of formula (I) in a total amount of 0.001 to 99.5% by weight, preferably 50 to 99% by weight, more preferably 80 to 95% by weight, especially 90 to 95% by weight, based on the total weight of the composition.

[0132] In particular, the composition comprises compounds of formula (I) in a total amount of 0.005 to 80% by weight, preferably 0.1 to 30% by weight, more preferably 1 to 20% by weight, especially 5 to 15% by weight, based on the total weight of the composition.

[0133] In particular, the composition comprises compounds of formula (I) in a total amount of 0.001 to 20% by weight, preferably 0.005 to 6% by weight, more preferably 0.05 to 4% by weight, especially 0.1 to 3% by weight, based on the total weight of the composition.

[0134] The terms Compound (I) and compound of formula (I) are used interchangeably throughout this specification. Also, the terms Compound (I) and compound of formula (I) are used interchangeably throughout this specification.

[0135] process: One embodiment of the invention claimed herein is a process for preparing a compound of formula (Ib), comprising at least a) A compound of formula (II) [ka] in the presence of an organometallic catalyst; b) optionally purifying the crude compound of formula (Ib) obtained in step (a), wherein R is a linear or branched C1-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl.

[0136] In one embodiment, the organometallic catalyst is bis(acetonitrile)dichloropalladium(II), tetrakis(triphenylphosphine)palladium, bis(acetato)bis(triphenylphosphine)palladium(II), bis(acetonitrile)palladium dichloride, bis(benzonitrile)palladium dichloride, 1,3-bis(2,6-diisopropylphenyl-imidazol-2-ylidene)gold(I) chloride, (acetonitrile)1,3-bis(2,6-diisopropylphenyl-imidazol-2-ylidene)gold(I) chloride, (acetonitrile) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) tetrafluoroborate, (acetonitrile) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) hexafluorophosphate, (acetonitrile) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) fluoroantimonic acid, or (acetonitrile) 1,3-di-tert-butylimidazol-2-ylidenegold(I) hexafluorophosphate.

[0137] In a preferred embodiment, the organometallic catalyst is selected from in situ formed catalyst complexes selected from bis(acetonitrile)dichloropalladium(II), tetrakis(triphenylphosphine)palladium, bis(acetato)bis(triphenylphosphine)palladium(II), bis(acetonitrile)palladium dichloride, bis(benzonitrile)palladium dichloride.

[0138] Preferably, the organometallic catalyst is bis(acetonitrile)dichloropalladium(II).

[0139] In a preferred embodiment, the organometallic catalyst is used in an amount of 0.001 to 0.3 weight equivalents relative to the compound of formula (II), preferably, 0.001 to 0.2 weight equivalents relative to the compound of formula (II), more preferably, 0.001 to 0.1 weight equivalents relative to the compound of formula (II), and even more preferably, 0.001 to 0.01 weight equivalents relative to the compound of formula (II).

[0140] In a preferred embodiment, the process is carried out for a time period of 3 to 30 hours, preferably for a time period of 3 to 24 hours, more preferably for a time period of 3 to 21 hours.

[0141] In a preferred embodiment, the reaction is carried out at room temperature.

[0142] Preferably, the process is carried out in the presence of a solvent, preferably selected from acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, 1,2-dichloroethane, benzene, toluene, isopropylbenzene, 1,3,5-trimethylbenzene, chlorobenzene, or ethylbenzene.

[0143] After the reaction is complete, the product can be isolated by conventional means and / or by removing the catalyst, for example by distillation, extraction or chromatographic techniques. If desired, the isolated product can then be further purified.

[0144] Embodiment Below, a list of embodiments is provided to further illustrate the present disclosure, but is not intended to limit the disclosure to the specific embodiments listed below.

[0145] 1. At least one compound of formula (I) [ka] or its stereoisomer (In the formula, R is a linear or branched C1-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl. Use of the compound of claim 1 for imparting a fragrance impression to a composition.

[0146] 2. The use of a compound of formula (I) as defined in embodiment 1, wherein R is selected from methyl, ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexyl, phenyl and 4-methylphenyl.

[0147] 3. The use of a compound of formula (I) as defined in embodiment 1, wherein R is methyl.

[0148] 4. The compound of formula (I) may be present in the form of a single stereoisomer, the cis isomer I(a) [ka] and Trans isomer I(b) [ka] The use of a compound of formula (I) according to any one of embodiments 1 to 3, comprising a ratio ranging from 0.01 to 99.99 to 99.99 to 0.01.

[0149] 5. A method for imparting a fragrance note to a composition, comprising at least the step of adding to the composition at least one compound of formula (I) as defined in any one of embodiments 1 to 4.

[0150] 6. The use or method according to any one of the preceding embodiments, wherein the composition is selected from a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition, or a crop protection composition.

[0151] 7. The use or method according to any one of the preceding embodiments, wherein the aromatic impression is selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes, or a combination of two or more notes.

[0152] 8. The use or method according to any one of the preceding embodiments, wherein the compound of formula (I) is present in a total amount ranging from 0.001% by weight to 70.0% by weight, based on the total weight of the composition.

[0153] 9. At least one compound of formula (I) according to embodiments 1 to 4, and (i) at least one aroma chemical (X) different from the compound of formula (I), or (ii) at least one non-aromatic chemical carrier; or A composition comprising both (i) and (ii).

[0154] 10. The composition of embodiment 9, wherein the compound of formula (I) is present in a total amount ranging from 0.001% by weight to 70.0% by weight, based on the total weight of the composition.

[0155] 11. The composition of embodiment 9, wherein the at least one non-fragrance chemical carrier (ii) is selected from a surfactant, an oil component, an antioxidant, a deodorant active, or a solvent.

[0156] 12. The composition according to any one of embodiments 9 to 10, wherein the composition is selected from a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition, or a crop protection composition.

[0157] 13. Compound of formula (I) [ka] or a stereoisomer thereof, During the ceremony, Compounds in which R is a linear or branched C2 to C9 alkyl, a linear or branched C2 to C9 alkenyl, a substituted or unsubstituted C4 to C8 cycloalkyl substituted with a C1 to C3 alkyl, or a substituted or unsubstituted aryl.

[0158] 14. Compound of formula (Ib) [ka] And, During the ceremony, Compounds in which R is a linear or branched C2 to C9 alkyl, a linear or branched C2 to C9 alkenyl, a substituted or unsubstituted C4 to C8 cycloalkyl substituted with a C1 to C3 alkyl, or a substituted or unsubstituted aryl.

[0159] 15. The compound according to embodiments 13-14, wherein R is selected from ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexyl, phenyl, and 4-methylphenyl.

[0160] 16. A process for preparing a compound of formula (Ib), comprising: a) A compound of formula (II) [ka] in the presence of an organometallic catalyst; b) optionally purifying the crude compound of formula (I) obtained in step (a), wherein R is a linear or branched C2-C9 alkyl, a linear or branched C2-C9 alkenyl, a substituted or unsubstituted C4-C8 cycloalkyl substituted with a C1-C3 alkyl, or a substituted or unsubstituted aryl.

[0161] 17. The process of embodiment 16, wherein the allylic rearrangement of step a) is carried out by stirring the reaction mixture for a time period between 3 hours and 21 hours.

[0162] 18. The process according to embodiment 16, wherein the process may optionally be carried out in the presence of a solvent.

[0163] 19. The process of embodiment 18, wherein the solvent is selected from acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, 1,2-dichloroethane, benzene, toluene, isopropylbenzene, 1,3,5-trimethylbenzene, chlorobenzene, or ethylbenzene.

[0164] 20. The organometallic catalyst is bis(acetonitrile)dichloropalladium(II), tetrakis(triphenylphosphine)palladium, bis(acetato)bis(triphenylphosphine)palladium(II), bis(acetonitrile)palladium dichloride, bis(benzonitrile)palladium dichloride, 1,3-bis(2,6-diisopropylphenyl-imidazol-2-ylidene)gold(I) chloride, (acetonitrile)1,3-bis(2,6-diisopropylphenyl)imidazole- 17. The process of embodiment 16, wherein the gold(I) tetrafluoroborate is selected from 2-ylidenegold(I) tetrafluoroborate, (acetonitrile) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) hexafluorophosphate, (acetonitrile) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) fluoroantimonic acid, and (acetonitrile) 1,3-di-tert-butylimidazol-2-ylidenegold(I) hexafluorophosphate.

[0165] 21. The process of embodiment 20, wherein the organometallic catalyst is bis(acetonitrile)dichloropalladium(II).

[0166] 22. The process according to any one of embodiments 16 to 21, wherein the organometallic catalyst is used in an amount of 0.001 to 0.3 weight equivalents relative to the compound of formula (II).

[0167] 23. A compound of formula (Ib'), [ka] Compound of formula (IIa) [ka] A compound containing the above in a range of 1.0% by weight to 0.01% by weight.

[0168] 24. At least one compound of formula (Ib') as defined in embodiment 23, and (i) at least one aroma chemical (X) different from the compound of formula (I), or (ii) at least one non-aromatic chemical carrier; or A composition comprising both (i) and (ii). EXAMPLES

[0169] The present invention will be described in detail by the following non-limiting examples. More specifically, the test methods specified below are part of the general disclosure of this application and are not limited to the specific examples.

[0170] 1. Analysis method: Common GC methods: Column: HP-5; 30m, 0.32ID, 0.25μmFD; Temperature program: 40℃, 5 min - 8℃ / min - 280℃ Flow rate: 1.0ml / min Injection: Split ratio: 100:1; Injection volume: 2.0 μl; Injection temperature: 250° C. Detector: FID, Temperature: 280℃; Characterization was performed by NMR: 1H-NMR and 13C-NMR. NMR spectra were measured on a Bruker DPX-500 spectrometer.

[0171] 2.Synthesis Example I: Synthesis of (E)-5-methylhex-2-enyl acetate Step 1: Synthesis of 5-methylhex-1-en-3-ol [ka] 1553 g of a 1 molar solution of vinylmagnesium bromide in THF (1.21 mol) was placed in a reactor. The solution was cooled to 0°C and a solution of 86.5 g (1.00 mol) of isovaleraldehyde in 264 ml of THF was added within 2.00 h to 2 h 20 min while maintaining the temperature at 0°C. The reaction mixture was warmed to 25°C within 1 h and quenched with 650 ml of saturated ammonium chloride solution. 500 ml of water was added to the mixture and the aqueous layer was separated and extracted three times with 500 ml of toluene each. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 1118 g of a ca. 6.9% solution of 5-methylhex-1-en-3-ol in toluene (GC-a-%).

[0172] Step 2: Synthesis of (3-methyl-1-vinyl-butyl) acetate [ka] 1117.8 g of a 6.9% solution of 5-methylhex-1-en-3-ol in toluene, 1.59 l of toluene and 12.27 g of DMAP were placed in a reactor and treated with 162.6 g (1.60 mol) of triethylamine. 114.3 g (1.46 mol) of acetyl chloride were added within 1 h at 25-30 °C. The mixture was stirred for another 1.5 h at 25 °C and quenched with 950 ml of saturated sodium bicarbonate solution. The aqueous layer was separated and the organic layer was washed two more times with sodium bicarbonate solution. The mixture was washed with 20% sulfuric acid and water and concentrated to obtain 178 g of a 60.4% solution in toluene.

[0173] Step 3: Synthesis of [(E)-5-methylhex-2-enyl]acetate [ka] To 177.8 g of crude (3-methyl-1-vinyl-butyl)acetate 60.4% solution in toluene, 1.5 l of THF and 6.7 g of bis(acetonitrile)dichloropalladium(II) were added and the mixture was stirred at room temperature for 3 h. The mixture was filtered and concentrated. The residue was dissolved in cyclohexane and filtered again on a silica gel column. The column was rinsed with cyclohexane and cyclohexane / ethyl acetate. The filtrate fractions were combined and concentrated to give 130 g of crude product containing starting material and product in a ratio of 1:5.6. The filtrate was concentrated again and distilled on a Vigreux column to give 45.7 g and 16.1 g of product with GC purities of 95.0% and 99.0%, respectively. NMR:13C-NMR(CDCl3,125MHz):169.9 ppm(s);134,3 ppm(d);123.8 ppm(d);64.3 ppm(t);40.5 ppm(t);27.1 ppm(d);21.2 ppm(q);21.2 ppm(q);20.0 ppm(q) 1H-NMR (CDCl3,500MHz): δ 5.75(dtr,1H),5.55(dtr,1H);4.52(d,2H);2.06(s,3H);1.95(tr,2H);1.59-1.71(m,1H);1.89(s,6H).

[0174] 3. Olfactory evaluation To test the quality and strength of the compounds and mixtures of the present invention, a scent strip test was conducted.

[0175] For this purpose, strips of absorbent paper were immersed in solutions containing 1-10% by weight of the compound to be tested in triethyl citrate. After evaporation of the solvent (approximately 30 seconds), the scent impression was evaluated by olfaction by a trained perfumer.

[0176] The fragrance impression of the compound of the present invention is shown in Table 1 below. The compound of the present invention is designated as Compound A and was formulated into a perfume composition according to Tables 2 and 3.

[0177] [Table 1]

[0178] 4. Advantageous Composition The compounds shown in Table 1 were formulated into compositions according to Tables 2 and 3. In Tables 2 and 3, the compounds in Table 1 are designated as "Compound A."

[0179] [Table 2]

[0180] [Table 3]

[0181] The compositions according to Tables 2 and 3, namely 1A, 1B, 2A, 2B, are deo pump spray, clean hair conditioner, face wash gel, foam bath concentrate, hair gel, self-foaming body wash, spray-type sun care emulsion, spray-type sun protection emulsion, emollient facial gel, two-phase oil foam bath, shampoo, shower bath, hydroalcoholic AP / deo pump spray, aerosol, hydroalcoholic AP / deo roll-on, styling gel type "out of bed" The composition may be included in various compositions selected from the group consisting of "Baby Shampoo for Sensitive Skin", "Baby Shampoo for Sensitive Skin", "Skin Care Shampoo for Sensitive Skin", "Shampoo for Sensitive Skin", "Bed", "Shaving Foam", "Baby Shampoo for Sensitive Skin", "Body Wash for Sensitive Skin", "Gloss Enhancing Shampoo for Sensitive Scalp", "Deodorant Stick", "Baby Wipes", "After Shave Balm", "Face Gel", "Face Day Care Cream", "Face Cleanser", "Body Lotion", "Sun Care SPF50+", "Spray Lotion", "Hand Dish Cleaner (Regular), Hand Dish Cleaner (Concentrate), Sanitary Cleaner (Concentrate), All-Purpose Cleaner, Antibacterial Fabric Softener, Detergent Composition, Powder Detergent Composition and Liquid Detergent Composition.

[0182] Those skilled in the art will be familiar with the various general formulations of the above mentioned products.

[0183] Compositions 1A, 1B, 2A and 2B can be combined in specific formulations, for example, as disclosed in IP.com Number: IPCOM000258614D, entitled New Aroma Chemicals, pages 6-46, Tables 1-D13, where "Fragrance Composition 1A" is replaced with an equal amount of Composition 1A, 1B, 2A, or 2B.

Claims

1. At least one compound of formula (I) 【Chemical 1】 or its stereoisomers (In the formula, R is a straight or branched C １ ~C ９ Alkyl, straight or branched C ２ ~C ９ Alkenyl, C １ ~C ３ Substituted or unsubstituted C substituted with alkyl ４ ~C ８ cycloalkyl, or substituted or unsubstituted aryl) Use of a compound of the formula (I) for imparting a fragrance impression to a composition.

2. 2. Use of at least one compound of formula (I) according to claim 1, wherein R is selected from methyl, ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexyl, phenyl, or 4-methylphenyl.

3. 2. Use of at least one compound of formula (I) according to claim 1, wherein R is methyl.

4. The compound of formula (I) may be present in the form of a single stereoisomer, the cis isomer I(a) 【Chemistry 2】 and Trans Isomer I(b) 【Chemistry 3】 in a weight ratio ranging from 0.01 to 99.99 to 99.99 to 0.

01.

5. 10. A method for imparting a fragrance note to a composition, comprising at least the step of adding to the composition at least one compound of formula (I) according to claim 1.

6. 6. The use or method according to any one of claims 1 to 5, wherein the aromatic impression is selected from fruity notes, green pear notes, apple notes, juicy fruity notes, styrax notes, pineapple notes, dusty notes, watery notes, or a combination of two or more notes.

7. 6. The use or method according to any one of claims 1 to 5, wherein the compounds of formula (I) are present in a total amount ranging from 0.001% to 70.0% by weight, based on the total weight of the composition.

8. At least one compound of formula (I) according to claims 1 to 4, and (i) at least one aroma chemical (X) different from the compound of formula (I); or (ii) at least one non-fragrance chemical carrier; or A composition comprising both (i) and (ii).

9. Compounds of formula (I) 【Chemistry 4】 or a stereoisomer thereof, During the ceremony, R is a straight or branched C ２ ~C ９ Alkyl, straight or branched C ２ ~C ９ Alkenyl, C １ ~C ３ Substituted or unsubstituted C substituted with alkyl ４ ~C ８ A compound that is a cycloalkyl, or a substituted or unsubstituted aryl.

10. A compound of formula (Ib) 【Chemistry 5】 During the ceremony, R is a straight or branched C ２ ~C ９ Alkyl, straight or branched C ２ ~C ９ Alkenyl, C １ ~C ３ Substituted or unsubstituted C substituted with alkyl ４ ~C ８ A compound that is a cycloalkyl, or a substituted or unsubstituted aryl.

11. 11. The compound of any one of claims 9 to 10, wherein R is selected from ethyl, propyl, isopropyl, 2-methylpropyl, cyclohexyl, methylcyclohexyl, phenyl, or 4-methylphenyl.

12. A process for preparing the compound of formula (Ib) according to claim 10, comprising: a) a compound of formula (II) 【Chemistry 6】 in the presence of an organometallic catalyst; b) optionally purifying the crude compound of formula (I) obtained in step (a), In the formula, R is a linear or branched C ２ ~C ９ Alkyl, straight or branched C ２ ~C ９ Alkenyl, C １ ~C ３ Substituted or unsubstituted C substituted with alkyl ４ ~C ８ The process is a cycloalkyl, or a substituted or unsubstituted aryl.

13. 13. The process of claim 12, wherein the allylic rearrangement of step a) is carried out by stirring the reaction mixture for a time period of from 3 hours to 21 hours.

14. The organometallic catalyst is selected from the group consisting of bis(acetonitrile)dichloropalladium(II), tetrakis(triphenylphosphine)palladium, bis(acetato)bis(triphenylphosphine)palladium(II), bis(acetonitrile)palladium dichloride, bis(benzonitrile)palladium dichloride, 1,3-bis(2,6-diisopropylphenyl-imidazol-2-ylidene)gold(I) chloride, and (acetonitrile)1,3-bis(2,6-diisopropylphenyl)imidazole- 13. The process of claim 12, wherein the fluorine-containing compound is selected from 2-ylidenegold(I) tetrafluoroborate, (acetonitrile)1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) hexafluorophosphate, (acetonitrile)1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) fluoroantimonic acid, or (acetonitrile)1,3-di-tert-butylimidazol-2-ylidenegold(I) hexafluorophosphate.

15. 15. The process of claim 14, wherein the organometallic catalyst is bis(acetonitrile)dichloropalladium(II).

16. The process according to any one of claims 12 to 15, wherein the organometallic catalyst is used in an amount of 0.001 to 0.3 weight equivalents relative to the compound of formula (II).

17. A compound of formula (Ib') 【Chemistry 7】 Compound of formula (IIa) 【Chemistry 8】 A compound containing the compound in the range of 1.0% by weight to 0.01% by weight.

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