Use of Cyclohomogeranate Esters as Aromatic Chemical Substances

Abstract

The present invention relates to the use of a compound of formula (I) as an aroma chemical for imparting to a composition a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a fresh note, a natural note, a ferny dill note, a camphoraceous note, or any arbitrary combination of two or more of these impressions, and also for improving and / or modifying the aroma of the composition. The present invention further targets a composition comprising at least one compound of formula (I) and (i) at least one aroma chemical different from the compound of formula (I), or (ii) at least one non-aromatic chemical carrier, or (iii) both (i) and (ii).

Description

Technical Field

[0001] The present invention relates to the use of compounds of formula (I) as aroma chemicals for imparting to a composition a woody note, a fruity note, a herbal note, a green note, a rooty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a fresh note, a natural note, a ferny note, a camphoraceous note, or any combination of two or more of these impressions, and also for improving and / or modifying the aroma of a composition. The present invention further relates 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), or (ii) at least one non-aromatic chemical carrier, or (iii) both (i) and (ii).

Background Art

[0002] Aroma chemicals, especially fragrances, have attracted great interest, particularly in the fields of cosmetics, cleaning and laundry compositions.

[0003] Despite the existence of a large number of synthetic aroma chemicals, new ingredients are constantly needed in order to be able to meet the numerous properties desired in a very diverse range of application fields. These include, firstly, sensory properties, i.e., the compounds need to have advantageous olfactory properties. Furthermore, aroma chemicals should also have further positive secondary properties, such as, for example, an efficient preparation method, the possibility of providing a better sensory profile as a result of a synergistic effect with other aroma chemicals, higher stability under specific application conditions, better and higher persistence, etc.

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

[0005] Among those that are particularly noteworthy are aroma chemicals that can impart one or more distinct sensory impressions to the composition, thereby contributing to a rich and interesting sensory profile, particularly the olfactory profile of the composition. In this regard, aroma chemicals that can impart a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an amber note, a fresh note, a natural note, a ferny dill note, a camphor-like note, or any combination of two or more of these impressions are mainly of interest. In addition, persistence and tenacity are of particular interest in the composition and in obtaining an odor impression that persists for a long time on the surface treated with the composition.

[0006] However, since even a slight change in the chemical structure can cause a large change in sensory properties such as odor and / or flavor, it is very difficult to search for substances having specific and distinct sensory properties such as a specific odor. Therefore, the search for new aroma chemicals is, in most cases, a difficult and laborious task without even knowing whether a substance having the desired odor and / or flavor will actually be found.

[0007] The object of the presently claimed invention is to provide, as aroma chemicals, substances that can be used alone or as a mixture in a composition, and in particular, strong odor substances having a pleasant odor are required. Furthermore, they need to be combinable with other aroma chemicals, enabling the generation of a novel and advantageous sensory profile and being usable in the composition. SUMMARY OF THE INVENTION

Problems to be Solved by the Invention

[0008] To provide a novel aroma chemical having a pleasant olfactory impression; preferably, a combination of two or more of the impressions selected from the group consisting of a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a natural note, a ferny note, a camphor-like note, or a fresh note is an object of the present invention.

[0009] A further object of the present invention is that the aroma chemicals must be obtainable from readily available starting materials so that their rapid and economical production is possible.

Means for Solving the Problems

[0010] These objects have been achieved by providing the compounds of the present invention and / or the mixtures of the present invention. Surprisingly, it has been found that the compounds of the present invention have a pleasant olfactory impression; preferably, a combination of two or more of the impressions selected from the group consisting of a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a natural note, a ferny note, a camphor-like note, or a fresh note.

[0011] A first aspect of the invention as presently claimed is a compound of formula (I) for imparting an aromatic impression to a composition

Chemical formula

[0012] A second aspect of the invention as presently claimed is for imparting an aroma impression to a composition, at least one compound of formula (Ia)

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0013] The third aspect of the presently claimed invention is at least one compound of formula (Ia) for imparting an aromatic impression to a composition

Chemical formula

Chemical formula

[0014] The fourth aspect of the presently claimed invention is for imparting an aromatic impression to a composition at least one compound of formula (Ia)

Chemical formula

Chemical formula

Chemical formula

[0015] A further aspect of the invention claimed in this specification relates to a method of imparting an aroma impression to a composition, which comprises at least the step of adding at least one compound of formula (I) to the composition.

[0016] Another aspect of the presently claimed invention relates to the use of at least one compound of formula (I) for modifying a composition having aromatic characteristics.

[0017] A further aspect of the invention is at least one compound of formula (Ib)

Chemical formula

Chemical formula

[0018] A further aspect of the invention is the compound of formula (Id)

Chemical formula

[0019] A further aspect of the presently claimed invention relates to a method of enhancing the aroma of a composition. The method comprises the step of mixing at least one compound of formula (I) with other components, such as at least one other aroma chemical different from the compound of formula (I) and / or at least one non-aroma chemical carrier, to obtain an aroma chemical composition.

[0020] Yet another aspect of the presently claimed invention relates to a method of modifying the aroma of a chemical composition. The method includes incorporating at least one compound of the presently claimed invention into an aroma chemical composition to obtain an aroma chemical composition having a modified aroma.

[0021] Furthermore, the compounds of formula (I) can be produced in good yields and purity by simple syntheses starting from readily available starting materials. Thus, the compounds of the presently claimed invention can be produced in large scale and in a simple and cost-effective manner.

DETAILED DESCRIPTION OF THE INVENTION

[0022] The following detailed description is illustrative in nature and is not intended to limit the presently claimed invention, or the uses and applications of the presently claimed invention. Further, there is no intention to be bound by the theories presented in the foregoing technical field, background, summary, or the following detailed description.

[0023] As used herein, the terms "comprising", "comprises" and "comprised of" are synonymous with "including", "includes" or "containing", "contains", and are inclusive or open-ended and do not exclude additional, unrecited members, elements or method steps. It should be understood that the terms "comprising", "comprises" and "comprised of" as used herein include the terms "consisting of", "consists" and "consists of".

[0024] Furthermore, terms such as "(a)", "(b)", "(c)", "(d)", etc. in the specification and claims are used to distinguish similar elements and are not necessarily used to describe an order or time sequence. Terms used in this way are interchangeable under appropriate circumstances, and it should be understood that embodiments of the subject matter described herein can be operated in an order other than that described or illustrated herein. For the sake of preparation, terms such as "(A)", "(B)", and "(C)" or "(AA)", "(BB)", and "(CC)" or "(a)", "(b)", "(c)", "(d)", "(i)", "(ii)", etc., when referring to steps of a method or use or assay, there is no consistency of time or time interval between the steps, i.e., the steps can be performed simultaneously, or, as described above or below in this specification, there can be a time interval of seconds, minutes, hours, days, weeks, months, or even years between such steps, unless otherwise indicated for the use.

[0025] In the following passages, various aspects of the subject matter are defined in more detail. Each aspect so defined can be combined with any other aspect, unless the contrary is clearly indicated. In particular, any feature shown to be preferred or advantageous can be combined with any other feature shown to be preferred or advantageous.

[0026] References to "one embodiment", "an embodiment", or "a preferred embodiment" throughout this specification mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the presently claimed invention. Thus, the appearances of the phrases "in one embodiment", "in a preferred embodiment", or "in a preferred embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, but may. Further, as will be apparent to those of ordinary skill in the art from this disclosure, in one or more embodiments, the features, structures, or characteristics may be combined in any suitable manner. Moreover, as will be understood by those 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 within the scope of the subject matter and mean different embodiments are formed. For example, in the appended claims, any combination of the claimed embodiments may be used.

[0027] Further, ranges defined throughout this specification include the end values as well, i.e., the range of 1 to 10 means both 1 and 10 are included within the range. To avoid doubt, Applicants reserve the right to obtain any equivalents in accordance with applicable law.

[0028] In the context of the present invention, the term "aromatic" refers to sensory characteristics and includes odor and / or flavor.

[0029] The term "aromatic chemical substance" means a substance used to obtain a sensory or organoleptic (used interchangeably herein) impression, including its use for obtaining 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, while the term "scent impression" or "perfume impression" or "aroma impression" (used interchangeably herein), when used herein, generally relates to an odor impression that is felt pleasant. Thus, "fragrance" or "scent" means an aromatic chemical substance that mainly induces a pleasant odor impression. Flavor means an aromatic chemical substance that induces a taste impression.

[0030] As used herein, the term "aromatic composition" refers to a composition that induces an aroma. The term "aromatic composition" includes "odor composition" and / or "flavor composition". An odor composition is a composition that mainly induces an odor impression, and a flavor composition is a composition that mainly induces a taste impression.

[0031] The term "aromatic profile" means the overall aroma impression of aromatic chemical substances and is composed of the individual aroma impressions of aromatic chemical substances. The term "odor composition" includes "fragrance composition" or "scent composition" (used interchangeably herein) that mainly induces an odor impression that is generally felt pleasant.

[0032] The general expressions "advantageous sensory properties" or "advantageous organoleptic properties" represent the niceness and conciseness of the sensory impressions conveyed by aroma chemicals. "Niceness" and "conciseness" are terms well known to those skilled in the art, such as perfumers. Niceness generally refers to a pleasant sensory impression that is spontaneously brought about and positively perceived. However, "being nice" does not necessarily mean the same as "sweet". "Being nice" can also be the smell of musk or sandalwood. "Conciseness" generally refers to a sensory impression that is spontaneously brought about and that brings about something that can be reproducibly and identically recalled as a particular something by the same test panelists. For example, if a substance has a smell that spontaneously makes one recall the smell of "apple", then that smell is clearly "apple". If this smell of apple is very pleasant, for example, because it makes one recall a sweet and ripe apple, then that smell is called "nice". However, typically the smell of a tart apple can also be clear. When smelling the smell of a substance, both reactions occur. In this example, if this results in a nice and clear smell of apple, then this substance has particularly advantageous sensory properties.

[0033] When referring in this specification to a composition, method or use of two compounds, the expressions "in combination", "in combination with" or "in combination with" are considered to take into account the fact that these two compounds need not be used in the form of a physical mixture of said compounds and can be used separately (e.g., added). When the compounds are used separately, they can be used (e.g., added) sequentially (i.e., one after the other) in any order or simultaneously (i.e., essentially at the same time).

[0034] The terms "boosting" or "boost" are used herein to denote the effect of enhancing and / or modifying the aroma of an aroma chemical or composition. The term "enhancing" includes improving the comfort and / or clarity of the aroma and / or improving its intensity. The term "modifying" includes changing the aroma profile. The terms "comfort" and "clarity" are well known to those skilled in the art, such as perfumers, and have their respective meanings.

[0035] Intensity can be determined by the determination of a threshold value. Although it is no longer necessary to define it, the odor threshold is the concentration of the substance in the relevant gas space at which a representative test panelist can still perceive the odor impression.

[0036] The boosting effect is particularly desired in fragrance compositions for applications characterized by top notes, for example in the field of taste in deodorants, air fresheners or chewing gums, where the odor is transmitted particularly rapidly and intensively.

[0037] The terms "the present invention relates to" and "the present invention is directed to" are used synonymously throughout the present invention.

[0038] The term "tenacity" represents the evaporation behavior of an aroma chemical over time. Tenacity can be determined, for example, by applying the aroma chemical to a test strip and subsequently evaluating the odor impression of the test strip olfactorily. In the case of an aroma chemical having a high tenacity, the time interval until a panelist can still distinguish the odor impression is longer.

[0039] The term "persistence" represents, in particular, the interaction of an aroma chemical with a surface, such as skin or a textile product, after subsequent treatment of the surface, such as washing. Persistence can be determined, for example, by washing a textile product with a textile detergent composition containing the aroma chemical and subsequently evaluating the textile product (wet textile product) immediately after washing and the dried textile product after long-term storage olfactorily.

[0040] The term "stability" refers to the behavior of an aroma chemical upon contact with oxygen, light, and / or other substances. A highly stable aroma chemical maintains its aroma profile over a long period of time, preferably under a wide variety of compositions and various storage conditions.

[0041] In order to impart a long-lasting aroma impression to a composition or to a surface treated with the composition, the tackiness, persistence, and stability of the aroma chemicals in the composition should preferably be high.

[0042] The term "C1-C5 alkyl" refers to a straight-chain or branched-chain alkyl group containing 1 to 5 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl (isopropyl), butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, and the like.

[0043] The term "C3-C5 alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon group having 3 to 5 carbon atoms and a double bond at any position. Examples are "C3-C5 alkenyl" groups such as 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, and the like.

[0044] The terms "cyclohomogeranate" and "ester of cyclohomogeric acid" are used herein with the same meaning.

[0045] As used herein, "compound(s) (I)" refers to the compound of formula (I), which includes all stereoisomeric forms (stereoisomers) thereof and / or salts thereof in any ratio.

[0046] As used herein, the term "mixture" refers to a mixture of at least one compound of formula (Ia) or a stereoisomer thereof or a stereoisomer; and / or at least one compound of formula (Ib) and / or a compound of formula (Ic).

[0047] The compounds of formula (Ia) and (1c) refer to the compound in its racemic form, or one of its enantiomerically pure forms (R or S), or a mixture of two possible enantiomers in any ratio, where the ratio of enantiomers ranges from 0.01:99.99 to 99.99:0.01.

[0048] The term "stereoisomer" is a general term described by the IUPAC and is used for all isomers of individual compounds that differ only in the orientation of atoms in space, not in the connectivity of atoms. Thus, the term stereoisomer includes enantiomers (mirror-image isomers), geometric isomers (cis / trans or E / Z) isomers, and diastereoisomers. For the exact definition of the terms, see the IUPAC definition or G. Helmchen: "Vocabulary and Nomenclature of Organic Stereochemistry" in Houben-Weyl E21a, Stereoselective Synthesis. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann (Hrsg.), 1995, 1-74. The possible isomers can exist as a mixture (i.e., a racemate, a cis / trans mixture, or a mixture of diastereoisomers).

[0049] Use One embodiment of the presently claimed invention is a compound of formula (I) for imparting an aromatic impression to a composition

Chemical formula

[0050] In one embodiment, the presently claimed invention is for imparting an aromatic impression to a composition, at least one compound of formula (Ia)

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0051] In another embodiment, the presently claimed invention is at least one compound of formula (Ia) for imparting an aroma impression to a composition

Chemical formula

Chemical formula

[0052] A further embodiment of the presently claimed invention is for imparting an aroma impression to a composition at least one compound of formula (Ia)

Chemical formula

Chemical formula

Chemical formula

[0053] In one embodiment, R is selected from methyl, ethyl, propyl, butyl, isobutyl, isopropyl, 1-propenyl, or 2-propenyl. Preferably, R is methyl, ethyl or 1-propenyl.

[0054] In one embodiment, the compound of formula (Ia) and the compound of formula (Ib) can be used alone or in admixture in any ratio.

[0055] In another embodiment, the mixture of the compound of formula (Ia) and the compound of formula (Ib) is a mixture in which the ratio of the compounds ranges from 0.1:99.9 to 99.9:0.1.

[0056] In another embodiment, the mixture of the compound of formula (Ia) and the compound of formula (Ib) is a mixture in which the ratio of the compounds ranges from 0.1:99.9 to 99.9:0.1, or any integer in the range of 0.1 to 99.9.

[0057] In another embodiment, the mixture of the compound of formula (Ia) and the compound of formula (Ib) is a mixture in which the ratio of the compounds ranges from 1:99 to 99:1. Preferably, it is within the range of 20:80 to 80:20, or within the range of 30:70 to 70:30, or within the range of 40:60 to 60:40.

[0058] In another embodiment, the mixture of the compound of formula (Ia) and the compound of formula (Ib) is a mixture in which the ratio of the compounds is 50:50.

[0059] Those skilled in the art can adjust the ratio of the compound of formula (Ia) and the compound of formula (Ib) to reach a specific ratio within the range of 0.1:99.9 to 99.9:0.1 and impart a specific aroma impression or some aroma impressions to the composition.

[0060] In one embodiment, the compound of formula (Ia) refers to the compound in its racemic form, or one of its enantiomerically pure forms (R or S), or a mixture of two possible enantiomers in any ratio, where the ratio of the enantiomers ranges from 0.01:99.99 to 99.99:0.01.

[0061] In another embodiment, the mixture has a ratio in the range of 90:10 to 99.9:0.1, where this ratio represents the total amount of the compound of formula (Ia) and the compound of formula (Ib) relative to the compound of formula (Ic).

[0062] In one embodiment, the mixture is [Compound of formula (Ia) + Compound of formula (Ib)]:[Compound of formula (Ic)] has a ratio in the range of 90:10 to 99.9:0.1, preferably in the range of 93:7 to 99:1, more preferably in the range of 95:5 to 99.9:0.1.

[0063] The preferred embodiments of the presently claimed invention are directed to the use of at least one compound of formula (I) as an aroma chemical that imparts to the composition a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a fresh note, a natural note, a ferny dill note, a camphoraceous note, or any combination of two or more thereof.

[0064] In a further embodiment, the presently claimed invention relates to the use of a compound of formula (I) for enhancing the aroma of a composition.

[0065] In an embodiment of the presently claimed invention, at least one compound of formula (I) is used as a fragrance or a fragrance composition.

[0066] In particular, at least one compound of formula (I) is used to impart to the composition a note selected from the group consisting of a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmet note, a sweet note, a vetiver note, an ionone note, an amber note, a fresh note, a natural note, a ferny note, a camphoraceous note, or a combination of two or more notes.

[0067] In one embodiment, the present invention relates to at least one compound of formula (Ib)

Chemical formula

Chemical formula

[0068] In another embodiment, the present invention relates to, for imparting an aroma impression to a composition, at least one compound of formula (Ib)

Chemical formula

Chemical formula

[0069] In one embodiment, R is methyl.

[0070] In one embodiment, a mixture of a compound of formula (Ib) and a compound of formula (IV), wherein the weight ratio of the compound of formula (Ib) to the compound of formula (IV) ranges from 90:10 to 99:1.

[0071] In one embodiment, the mixture of the compound of formula (Ib) and the compound of formula (IV) has an aromatic impression selected from leather or plastic or a combination thereof.

[0072] In one embodiment, the present invention relates to the use of a compound of formula (Id)

Chemical formula

[0073] In one embodiment, the present invention relates to the use of a compound of formula (Id)

Chemical formula

[0074] Preferably, the compound of formula (I) is

Chemical formula

[0075] The above-mentioned suitable compositions are, for example, compositions used in personal care, home care, industrial applications, and other applications such as pharmaceutical compositions or crop protection compositions.

[0076] In one embodiment, the compound of formula (I) comprises at least one compound of formula (Ia), at least one compound of formula (Ib), and at least one compound of formula (Ic), and the respective ratios of compounds Ia, Ib, and Ic can vary between 0.1 and 99.9.

[0077] Preferably, the compound of formula (I) according to the presently claimed invention is used in a composition selected from the group consisting of 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 fragrance dispensers, foods, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0078] The compositions are described in the following paragraphs.

[0079] Composition In one embodiment, the presently claimed invention relates to a composition comprising at least one compound of formula (I) 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 (iii) both (i) and (ii).

[0080] Preferably, in this embodiment, the composition comprises the compound of formula (I) in a total amount in the range of from 0.01% to 70.0% by weight, based on the total weight of the composition.

[0081] Preferably, the composition is an aroma composition, more preferably a perfume composition.

[0082] The aroma chemical is different from the compound of formula (I).

[0083] In one embodiment, the mixture comprises at least one aroma chemical different from the compound of formula (I). The aroma chemical different from the compound of formula (I) is also referred to as aroma chemical (X).

[0084] Due to their physical properties, the compounds of formula (I) can be successfully combined with aroma chemicals different from the compounds of formula (I) and other usual components in an aromatic composition, especially in an aroma composition. This enables the production of, for example, an aromatic composition (preferably, an aroma composition) having a novel and advantageous sensory profile. In particular, as already explained above, this compound can provide a potentiating effect on other aroma chemicals (such as fragrances).

[0085] The aroma chemical (X) is preferably: Geranyl acetate, α-hexyl cinnamaldehyde, 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, styrallyl 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, α-ionone, α-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-carboxaldehyde, α-amyl cinnamaldehyde, ethylene brassylate, (E)- and / or (Z)-3-methylcyclopentadeca-5-enone, 15-pentadeca-11-enolide and / or 15-pentadeca-12-enolide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethylocta-6-en-3-one, 2,Selected from the group consisting of 6-dimethyl-5-hepten-1-al, borneol, 3(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)-propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl)acetate, and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.,

[0086] In a preferred embodiment, at least one aromatic chemical substance (i) is selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, and methyl benzoate.,

[0087] In another preferred embodiment, at least one aromatic chemical substance (i) is selected from the group consisting of ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol), and 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0088] Additional aroma chemicals that can be combined with the compounds of the formula to obtain the compositions according to the presently claimed invention can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N.J., 1969, self - published or H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 4th Ed., Wiley - VCH, Weinheim 2016. Specifically, the following can be mentioned: extracts from natural raw materials, such as essential oils, concretes, absolutes, resins, resinous substances, balsams, tinctures, for example, ambergris tincture, amyris oil, angelica seed oil, angelica root oil, anise oil, valerian oil, basil oil, tree moss absolute, bay oil, mugwort oil, benzoin resin, bergamot oil, beeswax absolute, birch tar oil, bitter almond oil, savory oil, butyrylfou oil, cabreuva oil, cade oil, calamus oil, camphor oil, cananga oil, cardamom oil, cassia oil, cassia absolute, castoreum absolute, ceder leaf oil, ceder wood oil, cistus oil, citronella oil, lemon oil, copaiba balsam, copaiba balsam oil, coriander oil, costus root oil, cumin oil, hinoki oil, davana oil, dillweed oil, dillseed oil, Eau de brouts absolute, oak moss absoluteabsolute), elemi oil, tarragon oil, eucalyptus citriodora oil, eucalyptus oil, fennel oil, pine needle oil, galbanum oil, galbanum resin, geranium oil, grapefruit oil, guaiacwood oil, gurjun balsam, gurjun balsam oil, helichrysum absolute, helichrysum oil, ginger oil, iris root absolute, iris root oil, jasmine absolute, calamus 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, labege oil, lime oil distilled, lime oil pressed, linalool oil, litsea cubeba oil, bay leaf oil, mace oil, marjoram oil, mandarin oil, massoia bark oil, mimosa absolute (mimosaAbsolute, musk seed oil, musk tincture, clarissa oil, nutmeg oil, myrrh absolute, myrrh oil, ginger oil, clove leaf oil, clove flower oil, neroli oil, olibanum absolute, olibanum oil, opopanax oil, orange blossom absolute, orange oil, oregano oil, palmarosa oil, patchouli oil, palila oil, Peru balsam 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, star anise oil, egonoki oil, manjugiiku oil, fern needle oil, tea tree oil, terpineol oil, thyme oil, tolu balsam, tonka absolute, tuberose absolute, vanilla extract, violet leaf absolute, verbena oil, vetiver oil, juniper berry oil, wine lees oil, absan oil, wintergreen oil, hyssop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil, and their fractions, or components isolated therefrom, etc.

[0089] Individual fragrances from the group of hydrocarbons, for example, 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.

[0090] 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-methylenheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc.

[0091] 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, heptanal diethyl acetal, 1,1-dimethoxy-2,2,5-trimethyl-4-hexene, citronellyloxyacetaldehyde, (E / Z)-1-(1-methoxypropoxy)-hex-3-ene, etc., aliphatic ketones and their oximes, such as 2-heptanone, 2-octanone, 3-octanone, 2-nonanone, 5-methyl-3-heptanone, 5-methyl-3-heptanone oxime, 2,4,4,7-tetramethyl-6-octen-3-one, 6-methyl-5-hepten-2-one, etc.

[0092] Aliphatic sulfur-containing compounds, such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, 1-menthene-8-thiol, etc.

[0093] Aliphatic nitriles, such as 2-nonenitrile, 2-undecenenitrile, 2-tridecenenitrile, 3,12-tridecadienenitrile, 3,7-dimethyl-2,6-octadienenitrile, 3,7-dimethyl-6-octenenitrile, etc.

[0094] Esters of aliphatic carboxylic acids, such as (E) and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, hexyl acetate, 3,5,5-trimethylhexyl acetate, 3-methyl-2-butenyl acetate, (E)-2-hexenyl acetate, (E) and (Z)-3-hexenyl acetate, octyl acetate, 3-octyl acetate, 1-octen-3-yl acetate, ethyl butyrate, butyl butyrate, isoamyl butyrate, hexyl butyrate, (E) and (Z)-3-hexenyl isobutyrate, hexyl crotonate, ethyl isovalerate, ethyl 2-methylpentanoate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, allyl heptanoate, ethyl octanoate, ethyl (E,Z)-2,4-decadienoate, methyl 2-octynoate, methyl 2-nonynoate, allyl 2-isoamyloxyacetate, methyl-3,7-dimethyl-2,6-octadienoate, 4-methyl-2-pentyl crotonate, etc.

[0095] 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-octatriene-3-ol, 2,6-dimethyl-2,5,7-octatriene-1-ol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates, etc.

[0096] Acyclic terpene aldehydes and ketones, such as geranial, neral, citronellal, 7-hydroxy-3,7-dimethyloctanal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranylacetone, and dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal, etc., cyclic terpene alcohols, such as menthol, isopulegol, α-terpineol, terpinene-4-ol, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambrinol, vetiverol, guaiol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates, etc.

[0097] Cyclic terpene aldehydes and ketones, such as menthone, isomenthone, 8-mercaptomenthan-3-one, carvone, camphor, fenchone, α-ionone, β-ionone, α-n-methyliorone, β-n-methyliorone, α-isomethyliorone, β-isomethyliorone, α-irone, α-damascone, β-damascone, β-damasconone, 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-cinenal, β-cinenal, acetylated cedrol oil (methyl cedryl ketone), etc.

[0098] 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.

[0099] 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.

[0100] cyclic and alicyclic ethers, such as cineole, cedryl methyl ether, cyclododecyl methyl ether, 1,1-dimethoxycyclododecane, (ethoxymethoxy)cyclododecane, α-cedrene epoxide, 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 3a-ethyl-6,6,9a-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.

[0101] Cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-heptylcyclopentanone, 2-pentylcyclopentanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one, 3-methyl-2-pentyl-2-cyclopenten-1-one, 3-methyl-4-cyclopentadecenone, 3-methyl-5-cyclopentadecenone, 3-methylcyclopentadecanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 4-tert-pentylcyclohexanone, 5-cyclohexadecen-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 8-cyclohexadecen-1-one, 7-cyclohexadecen-1-one, (7 / 8)-cyclohexadecen-1-one, 9-cycloheptadecen-1-one, cyclopentadecanone, cyclohexadecanone, etc.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate, etc.

[0106] 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-cyclohexene-carboxylate, ethyl 2-methyl-1,3-dioxolane-2-acetate, etc.

[0107] 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.

[0108] 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.

[0109] 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-dioxane, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxane, etc.

[0110] 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.

[0111] Aromatic and araliphatic ketones, such as acetophenone, 4-methylacetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthalenyl)-ethanone, 2-benzofuranylethanone, (3-methyl-2-benzofuranylethanone), benzophenone, 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone, 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone, 5’,6’,7’,8’-tetrahydro-3’,5’,5’,6’,8’,8’-hexamethyl-2’-acetonaphthone, etc.

[0112] Aromatic and aliphatic carboxylic acids and their esters, for example, benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenylacetate, ethyl phenylacetate, geranyl phenylacetate, phenylethyl phenylacetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, cinnamyl cinnamate, allyl phenoxyacetate, methyl salicylate, 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.

[0113] Nitrogen-containing aromatic compounds, for example, 2,4,6-trinitro-1,3-dimethyl-5tert-butylbenzene, 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone, cinnamitrile, 3-methyl-5-phenyl-2-pentenonitrile, 3-methyl-5-phenylpentanonitrile, methyl anthranilate, methyl-N-methylanthranilate, 7-hydroxy-3,7-dimethyloctanal, Schiff base of methyl anthranilate with 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde, 6-isopropylquinoline, 6-isobutylquinoline, 6-sec-butylquinoline, 2-(3-phenylpropyl)pyridine, indole, skatole, 2-methoxy-3isopropyl-pyrazine, 2-isobutyl-3-methoxypyrazine, etc.

[0114] 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 phenylacetate, etc.

[0115] 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.

[0116] Lactones, such as 1,4-octanolide, 3-methyl-1,4-octanolide, 1,4-nonanolide, 1,4-decanolide, 8-decen-1,4-olide, 1,4-undecanolide, 1,4-dodecanolide, 1,5-decanolide, 1,5-dodecanolide, 4-methyl-1,4-decanolide, 1,15-pentadecanolide, cis and trans-11-pentadecen-1,15-olide, cis and trans-12-pentadecen-1,15-olide, 1,16-hexadecanolide, 9-hexadecen-1,16-olide, 10-oxa-1,16-hexadecanolide, 11-oxa-1,16-hexadecanolide, 12-oxa-1,16-hexadecanolide, ethylene 1,12-dodecanedioate, ethylene 1,13-tridecanedioate, coumarin, 2,3-dihydrocoumarin, octahydrocoumarin, tetrahydroactinidolide, etc.

[0117] The aroma chemical (X) used in the composition is obtained from known commercial sources and procured from Germany.

[0118] In a preferred embodiment, the composition comprises at least one compound of formula (I) and at least one aromatic chemical substance (X).

[0119] In another preferred embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), and at least one aromatic chemical substance (X).

[0120] Non-aromatic chemical carrier: The non-aromatic chemical carrier in the composition of the present invention is preferably selected from the group consisting of surfactants, oil components, antioxidants, deodorant activators, and solvents.

[0121] Preferably, at least one non-aromatic chemical carrier is a compound, a mixture of compounds, or other additives that have no sensory properties or no notable sensory properties. The non-aromatic chemical carrier, when included in the composition, can serve to dilute and / or fix the compound of formula (I) and, optionally, at least one aromatic chemical substance (X) as defined above.

[0122] The non-aromatic chemical carrier in the composition of the present invention is preferably selected from the group consisting of surfactants, oil components, solvents, or any mixture of two or more of the foregoing.

[0123] Solvent In the context of the presently claimed invention, the "solvent" serves to dilute the compound of formula (I) used in accordance with the present invention that has no aroma of its own.

[0124] The amount of the solvent is selected according to the composition.

[0125] Preferably, the solvent is present in the composition in a total amount of 0.01% to 99.0% by weight, more preferably 0.05% to 95.0% by weight, even more preferably 0.1% to 80.0% by weight, most preferably 0.1% to 70.0% by weight, and particularly 0.1% to 60.0% by weight, based on the total weight of the composition.

[0126] In a preferred embodiment, the composition comprises a total solvent in an amount of 0.05% to 10% by weight, more preferably 0.1% to 5% by weight, even more preferably 0.2% to 3% by weight, based on the total weight of the composition. In yet another preferred embodiment of the present invention, the composition comprises a total solvent in an amount of 20% to 70% by weight, more preferably 25% to 50% by weight, based on the total weight of the composition.

[0127] Preferred solvents are selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2 - butylene glycol, dipropylene glycol, triethyl citrate, isopropyl myristate, and any mixture of two or more of the foregoing.

[0128] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one solvent, and optionally at least one aromatic chemical (X).

[0129] In another preferred embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), at least one solvent, and optionally at least one aromatic chemical (X).

[0130] Oil component Preferably, the total oil component is present in an amount of 0.1 to 80% by weight, more preferably 0.5 to 70% by weight, even more preferably 1 to 60% by weight, even more preferably 1 to 50% by weight, particularly 1 to 40% by weight, more particularly 5 to 25% by weight, especially 5 to 15% by weight, based on the total weight of the composition.

[0131] Preferably, the oil component is selected from geranylgeraniol based on aliphatic 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, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, and erucyl erucate.Also, esters of C18-C38 alkyl-hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, more specifically, dioctyl maleate, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g., propylene glycol, dimer diol or trimer triol), triglycerides based on C6-C10 fatty acids, liquid mono-, di- and triglyceride mixtures based on C6-C18 fatty acids, esters of C6-C22 fatty alcohols and / or geraniol with aromatic carboxylic acids, more specifically, esters of dicarboxylic acids with polyols containing 2-10 carbon atoms and 2-6 hydroxyl groups, such as benzoic acid, plant oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates, e.g., dicaprylyl carbonate (Cetiol® CC), etc., geranyl carbonates based on fatty alcohols containing 6-18, preferably 8-10 carbon atoms, esters of benzoic acid with linear and / or branched C6-C22 alcohols (e.g., Finsolv® TN), linear or branched symmetric or asymmetric dialkyl ethers containing 6-22 carbon atoms per alkyl group, e.g., dicaprylyl ether (Cetiol® OE), etc., ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof are preferred.

[0132] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one oil component, and optionally at least one aromatic chemical (X).

[0133] In another preferred embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), at least one oil component, and optionally at least one aromatic chemical (X).

[0134] Antioxidant It will be appreciated that antioxidants can inhibit or prevent undesirable changes in the composition to be protected caused by the oxygen effect and other oxidation processes. In most cases, the effect of antioxidants is to act as free radical scavengers against free radicals generated during auto-oxidation.

[0135] In a preferred embodiment, the antioxidant is selected from the group consisting of: · Amino acids (e.g., glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives, · Imidazole (e.g., urocanic acid) and its 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 their derivatives, · 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, γ-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-, heptathionine sulfoximine), · (Metal) chelating agents (e.g., α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), · α-hydroxy acids (e.g., citric acid, lactic acid, malic acid), · humic acid, bile acids, bile extracts, bilirubin, biliverdin, boldine (= alkaloid derived from the plant Peumus boldus, bold extract), · EDTA, EGTA and their derivatives, · unsaturated fatty acids and their derivatives (e.g., γ-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), · coniferyl benzoate of benzoin gum, rutinic acid and its derivatives, α-glycosylrutin, ferulic acid, furfurylidene glucitol, · butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), · nordihydroguaiaretic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and their 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). And mixtures of two or more of the foregoing.

[0136] In a preferred embodiment, the antioxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl-hydroxylhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ascorbyl palmitate, tocopherol, and mixtures of two or more of the foregoing.

[0137] Preferably, the composition according to the presently claimed invention comprises the antioxidant in a total amount of from 0.001 to 25% by weight, preferably from 0.005 to 10% by weight, more preferably from 0.01 to 8% by weight, even more preferably from 0.025 to 7% by weight, and even more preferably from 0.05 to 5% by weight, based on the total weight of the composition.

[0138] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one antioxidant, and optionally at least one aromatic chemical (X).

[0139] In another preferred embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), at least one antioxidant, and optionally at least one aromatic chemical (X).

[0140] Deodorizing active agent The deodorizing composition (deodorant and antiperspirant) neutralizes, masks, or removes body odor. Body odor is generated by the action of skin bacteria on apocrine sweat, resulting in the formation of unpleasant-smelling decomposition products.

[0141] Preferably, the deodorizing active agent is selected from the group consisting of antiperspirants, esterase inhibitors, antibacterial agents, and mixtures of two or more of the foregoing.

[0142] Suitable antiperspirants are selected from the group consisting of salts of aluminum, zirconium or zinc. Examples include aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, and their composite compounds with, for example, 1,2-propylene glycol, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and their composite compounds with amino acids such as glycine. Aluminum chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and their composite compounds are preferably used.

[0143] Preferably, the antiperspirant is selected from the group consisting of aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and mixtures of two or more of the foregoing.

[0144] When sweat is present in the underarm area, extracellular enzymes, mainly proteases and / or lipases, are formed by bacteria, which break down the esters present in the sweat, releasing an 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. The esterase inhibitor inhibits the enzyme activity, thereby reducing the generation of odor. When the citrate ester is cleaved, presumably free acid is released, and the skin pH value drops to the extent that the enzyme is 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.

[0145] Preferably, the esterase inhibitor is selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester, zinc glycinate and mixtures of two or more of the foregoing.

[0146] Preferably, the composition according to the presently claimed invention contains an esterase inhibitor in a total amount in the range of 0.01 to 20% by weight, preferably 0.1 to 10% by weight, more specifically 0.5 to 5% by weight, based on the total weight of the composition.

[0147] As used herein, the term "antibacterial agent" encompasses substances having bactericidal and / or bacteriostatic properties. Typically, these substances, for example, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), etc., for example, salicylic acid-N-alkylamides such as salicylic acid-n-octylamide or salicylic acid-n-decylamide, etc., act against Gram-positive bacteria.

[0148] Preferably, the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamide, and mixtures of two or more of the foregoing.

[0149] Preferably, the composition according to the presently claimed invention contains the antibacterial 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.

[0150] In a preferred embodiment, the composition comprises at least one compound of formula (I), at least one deodorizing active agent, and optionally at least one aromatic chemical (X).

[0151] In another preferred alternative embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), at least one deodorizing active agent, and optionally at least one aromatic chemical (X).

[0152] Surfactant Preferably, the surfactant is selected from the group consisting of anionic, nonionic, cationic, amphoteric, zwitterionic surfactants, and mixtures of two or more of the foregoing. More preferably, the surfactant is an anionic surfactant.

[0153] Preferably, the composition according to the present invention contains a surfactant in a total amount of 0 to 40% by weight, more preferably 0 to 20% by weight, still more preferably 0.1 to 15% by weight, particularly 0.1 to 10% by weight, based on the total weight of the composition.

[0154] Suitable 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 (alkenyl) 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 surfactant contains a polyglycol ether chain, these can have a conventional homolog distribution, but preferably have a narrow range of homolog distribution.

[0155] A zwitterionic surfactant is a surfactant compound containing at least one quaternary ammonium group and at least one COO(−) or SO3(−) group in the molecule.

[0156] Particularly preferred zwitterionic surfactants are so-called betaines, for example, N-alkyl-N,N-dimethylammonium glycinate, such as cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, such as cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoline containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethylhydroxyethylcarboxymethyl glycinate. Fatty acid amide derivatives known by the CTFA name of cocamidopropyl betaine are particularly preferred.

[0157] Amphoteric surfactants are also particularly suitable as surfactant aids. Amphoteric surfactants are surfactant compounds that contain, in addition to an alkyl or acyl group of C8 - C18, at least one free amino group and at least one -COOH or SO3H group in the molecule and can form an inner salt. Examples of suitable amphoteric surfactants are N-alkyl glycine, N-alkyl propionic acid, N-alkyl aminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropyl glycine, N-alkyl taurine, N-alkyl sarcosine, 2-alkylaminopropionic acid, and alkylaminoacetic acid containing about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate, and acyl sarcosine.

[0158] Anionic surfactants are characterized by water-soluble anionic groups such as carboxylate, sulfate, sulfonate, or phosphate groups and lipophilic groups. Dermatologically safe anionic surfactants are known to many practitioners from relevant textbooks and are commercially available. They are, in particular, alkyl sulfates in the form of their alkali metal, ammonium salts or alkanolammonium salts, alkyl ether sulfates, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, acyl taurines containing linear C12-C18 alkyl or acyl groups, and sulfosuccinates, and acyl glutamates in the form of their alkali metal or ammonium salts.

[0159] Particularly preferred cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more specifically 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, readily biodegradable quaternary ester compounds such as dialkylammonium methosulfate and methylhydroxyalkyldialkyloxyalkylammonium methosulfate marketed under the name Stepantexe and the corresponding products of the Dehyquart® series can be used as cationic surfactants. "Esterquats" are generally understood to be quaternized fatty acid triethanolamine ester salts. These can impart a specific softness to the composition. They are known substances prepared by relevant methods of organic chemistry. Other cationic surfactants suitable for use according to the present invention are quaternized protein hydrolysates.

[0160] Due to the characteristic sensory properties, persistence, tackiness, and stability of the compound of formula (I), it can be particularly used, for example, in surfactant-containing compositions such as detergents (especially laundry care products and all-purpose cleaners), to impart an odor, preferably an impression of a fragrance. Preferably, a long-lasting woody note, fruity note, herbal note, green note, rutty note, citrus note, petitgrain note, floral note, damascone note, tobacco note, ashtray note, gourmand note, sweet note, ionone note, amber note, fresh note, natural note, ferny dill note, camphor-like note, vetiver note can be used to impart to a composition containing a surfactant.

[0161] 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).

[0162] In another preferred embodiment, the composition comprises at least one compound of formula (Ia), at least one compound of formula (Ib), at least one compound of formula (Ic), at least one surfactant, and optionally at least one fragrance chemical (X).

[0163] 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 fragrance dispensers, foods, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0164] The perfume composition can be selected from fine fragrances, deodorants in liquid form, gel form or applied to a solid carrier, aerosol sprays, fragrance cleaners, perfume candles, and oils such as lamp oils or massage oils.

[0165] Examples of fine fragrances are perfume extracts, eau de parfum, eau de toilette, eau de cologne, eau de solide, and extrait parfum.

[0166] The body care composition includes cosmetic compositions and oral and dental hygiene products, such as aftershave, pre-shave products, splash cologne, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, water-in-oil, oil-in-water, and water-in-oil-in-water type cosmetic emulsions, such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, sun protection creams and lotions, etc., hair care products, such as hair sprays, hair gels, setting lotions, hair conditioners, hair shampoos, permanent and semi-permanent hair colorants, cold waves and hair smoothing compositions, etc., hair shaping compositions, hair tonics, hair creams and hair lotions, etc., deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, etc., decorative cosmetic products, such as eyeliners, eyeshadows, manicures, makeup supplies, lipsticks and mascaras, etc., and oral and dental hygiene products, such as toothpastes, dental floss, mouthwashes, bad breath removers, dental foams, dental gels, and dental strips, etc., and can be selected from these.

[0167] The hygiene products can be selected from incense, insecticides, repellents, propellants, rust removers, perfumed freshening wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, pocket tissues, dishwashing detergents, and deodorants.

[0168] Cleaning compositions, such as detergents for solid surfaces, can be selected from perfumed scents, acidic, alkaline, and neutral detergents, such as floor detergents, window detergents, dishwashing compositions for both hand and machine washing, bathroom and sanitary detergents, refined milk, solid and liquid toilet detergents, powder and foamed carpet detergents, waxes and polishes such as furniture polish, floor wax, shoe cream, disinfectants, surface disinfectants and sanitary detergents, brake detergents, pipe detergents, water stain removers, grill and oven detergents, algae and moss removers, mold removers, facade cleaners.

[0169] Fiber product detergent compositions can be selected from liquid detergents, powder detergents, bleaches, pre-washing agents such as soaking agents and stain removers, fabric softeners, laundry soaps, and laundry tablets.

[0170] Food means raw, cooked, or processed edible substances, ice, beverages, or ingredients, all or part of which are used or intended for use by humans for consumption, or chewing gum, gummy candies, jelly, and confectionery.

[0171] Dietary supplements are products intended for ingestion that contain dietary ingredients intended to add further nutritional value to the diet. Dietary ingredients can be one or any combination of the following substances: vitamins, minerals, herbs or other plants, amino acids, food substances that people use to supplement their diet by increasing their total dietary intake, concentrates, metabolites, components, or extracts. Dietary supplements can be found in many forms, such as tablets, capsules, soft gels, gel caps, liquids, or powders.

[0172] Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment, or prevention of diseases, as well as articles (other than food) intended to affect the structure or any function of the body of a human or other animal.

[0173] Crop protection compositions include compositions intended for the management of plant diseases, weeds and other pests (both vertebrate and invertebrate) that damage crops and forests.

[0174] Preferably, the composition according to the invention is an antiseptic, abrasive, anti-acne agent, agent for combating skin ageing, anti-cellulite agent, anti-dandruff agent, anti-inflammatory agent, inflammation inhibitor, irritation reliever, astringent, antiperspirant, antiseptic, antistatic agent, binder, buffer, carrier material, chelating agent, cell stimulant, care agent, depilatory, emulsifier, enzyme, essential oil, fibre, film-forming agent, fixative, foaming agent, foam stabilizer, foam inhibitor, foam promoter, bactericide, gelling agent, gel-forming agent, hair care agent, hair styling agent, hair conditioner, moisture provider, humectant, wetting agent, bleaching agent, strengthening agent, deodorant, fluorescent brightening agent, impregnating agent, antifouling agent, friction reducer, lubricant, moisturizing cream, ointment, milky agent, plasticizer, coating agent, polishing agent, gloss agent, polymer, powder, protein, refatting agent, keratolytic agent, silicone, skin soother, skin cleanser, skin care agent, skin healing agent, skin whitening agent, skin protecting agent, skin softening agent, cooling agent, skin cooling agent, warming agent, skin warming agent, stabilizer, UV absorber, UV filter, softening agent, suspending agent, sunburn protector for skin, thickening agent, vitamin, wax, fat, phospholipid, saturated fatty acid, mono- or polyunsaturated fatty acid, α-hydroxy acid, polyhydroxy fatty acid, liquefying agent, dye, color protection agent, pigment, anticorrosive agent, polyol, electrolyte, and at least one adjuvant selected from the group consisting of silicone derivatives.

[0175] A method for preparing a composition for imparting an aromatic impression to a composition and a method for imparting an aromatic impression to a composition

[0176] One embodiment of the present invention is: (i) at least one aroma chemical (X) other than the compound according to the invention, or (ii) at least one non-aromatic chemical carrier, or A method for preparing a composition of a compound of formula (I) comprising both (i) and (ii).

[0177] The present invention also relates to a method for enhancing the olfactory impression of a composition, which method comprises incorporating at least one compound of formula (I) into the composition.

[0178] In particular, the present invention relates 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 fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition or a crop protection composition, which method comprises incorporating at least one compound of formula (I) in a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0179] In one embodiment, the present invention relates to a method for imparting to a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition or a crop protection composition a note that evokes elements of a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an ambre note, a fresh note, a natural note, a ferny dill note, a camphoraceous note, which method comprises incorporating at least one compound of formula (I) in a perfume composition, a body care composition, a hygiene product, a cleaning composition, a textile detergent composition, a composition for a fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0180] amount Generally, the total amount of the compound of formula (I) in the compositions, methods and uses according to the invention will typically be adapted to the particular intended use or application and can thus vary widely. As a rule, aroma chemicals, preferably in the normal standard commercial amounts of fragrances, are used.

[0181] Preferably, the composition according to the present invention contains 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. In particular, the composition contains 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.

[0182] In particular, the composition contains the compound 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.

[0183] In particular, the composition contains the compound 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.

[0184] The terms "compound (I)" and "compounds of formula (I)" are used throughout this specification to have the same meaning. Also, the terms "compounds (I)" and "compounds of formula (I)" are used throughout this specification to have the same meaning.

[0185] Embodiments The following provides a list of embodiments for further exemplifying the present disclosure, but is not intended to limit the present disclosure to the specific embodiments listed below.

[0186] 1. At least one compound of formula (I) for imparting an aromatic impression to the composition

Chemical formula

[0187] 2. The compound of formula (I) is at least one compound of formula (Ia)

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0188] 3. Use according to embodiment 1 or 2, wherein R is selected from methyl, ethyl, propyl, butyl, isobutyl, isopropyl, 1-propenyl, or 2-propenyl.

[0189] 4. Use according to any one of embodiments 1 to 3, wherein R is selected from methyl, ethyl, or 1-propenyl.

[0190] 5. Use of the mixture according to embodiments 2 to 4, wherein the weight ratio of at least one compound of formula (Ia) and at least one compound of formula (Ib) is in the range of 0.1:99.9 to 99.9:0.1.

[0191] 6. Use of the mixture according to any one of embodiments 2 to 5, wherein the weight ratio of at least one compound of formula (Ia) and at least one compound of formula (Ib) is in the range of 20:80 to 80:20, preferably 30:70 to 70:30, or preferably 40:60 to 60:40, or preferably 50:50.

[0192] 7. Use of the mixture according to any one of embodiments 2 to 6, wherein the mixture has a ratio in the range of 90:10 to 99.9:0.1, and the ratio represents the total amount of the compound of formula (Ia) and the compound of formula (Ib) relative to the compound of formula (Ic).

[0193] 8. A method for imparting an aroma impression to a composition, comprising at least the step of adding at least one compound of formula (I) according to any one of embodiments 1 to 7 to the composition.

[0194] 9. Use or method according to any one of embodiments 1 to 8, wherein the aroma impression is selected from the group consisting of a woody note, a fruity note, a herbal note, a green note, a rutty note, a citrus note, a petitgrain note, a floral note, a damascone note, a tobacco note, an ashtray note, a gourmand note, a sweet note, a vetiver note, an ionone note, an amber note, a fresh note, a natural note, a ferny dill note, a camphor-like note, or any combination of two or more of these notes.

[0195] 10. Use or method according to any one of embodiments 1 to 8, wherein at least one compound of formula (I) is present in a total amount in the range of 0.001% by weight or more to 70.0% by weight or less, based on the total weight of the composition.

[0196] 11. i) at least one compound of formula (Ib) according to any one of embodiments 1 to 7, and ii) at least one aromatic chemical substance (X) different from the compound of formula (I), or iii) at least one non-aromatic chemical carrier, or iv) both (ii) and (iii), a composition comprising.

[0197] 12. Composition according to embodiment 11, wherein at least one compound according to embodiments 1 to 7 is present in the range of 0.01% by weight or more to 70.0% by weight or less, based on the total weight of the composition.

[0198] 13. Composition according to embodiment 11, wherein at least one non-aromatic chemical carrier (ii) is selected from a surfactant, an oil component, an antioxidant, a deodorizing activator, or a solvent.

[0199] 14. Composition according to any one of embodiments 11 to 13, 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 fragrance dispenser, a food, a dietary supplement, a pharmaceutical composition, or a crop protection composition.

[0200] 15. At least one compound of formula (Ib)

Chemical formula

Chemical formula

[0201] 16. Use of the mixture according to embodiment 15 for imparting an aromatic impression to a composition.

[0202] 17. A method for imparting an aromatic impression to a composition, the method comprising at least the step of adding the mixture according to embodiment 15 to the composition.

[0203] 18. The mixture, or use or method according to any one of embodiments 15-17, wherein the weight ratio of the compounds of formula (Ib) and (IV) is in the range of 90:10 to 99:1.

[0204] 19. The use or method according to any one of embodiments 16-18, wherein the aromatic impression is selected from leather or plastic or a combination thereof.

[0205] 20. A method for preparing a mixture of at least one compound of formula (I) according to any one of embodiments 1-7, a) Using a catalytic amount of an acid, a compound of formula (III)

Chemical formula

Examples

[0206] The present invention is illustrated 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 specific examples.

[0207] 1. Analytical methods and materials: Materials: Chemical substances: The chemical substances were purchased from vendors (ABCR, Acros Organics, Alfa Aesar, Apollo Scientific, Fluorochem, Manch Organics, Sigma-Aldrich, TCI) and used without further purification unless otherwise specified.

[0208] Analysis methods: NMR spectroscopy: The property evaluation was 13 performed by 1 13C NMR and 13 1H NMR. 1 The 13C NMR and 1H NMR spectra were measured on a Bruker AV-500 spectrometer.

[0209] (Flash) column chromatography (Flash) column chromatography was carried out using silica gel (60 Å, 230 - 400 mesh, particle size: 43 - 63 μm) from Merck or a distilled industrial brand solvent. The solvent mixture and volume ratio (v / v) used as the mobile phase for chromatography were specified in the corresponding experiment. Flash column chromatography was carried out in a glass column by applying a slightly elevated air or argon (0.3 mbar) pressure.

[0210] Gas chromatography (GC) Gas chromatography (GC) was carried out using HP6890 and 5890 series instruments equipped with a split-mode capillary injection system and a flame ionization detector (FID), using hydrogen (H2) as the carrier gas.

[0211] 2. Synthesis Example 1: Preparation of α-methyl cyclogelerate (α-1), β-methyl cyclohomogelerate (β-1), γ-methyl cyclogelerate (γ-1) [Chemical formula] In a 250 mL reactor (equipped with a flow breaker, an impeller stirrer, a condenser, and an Ar inert gas connection), methyl homogeranate (53 g, total E / Z-isomers 97.65%, 0.264 mol) was dissolved in toluene (120 mL) and heated to 100 °C. The solution was stirred vigorously, and a catalytic amount of H3PO4 (85%, 4.4 g) was added via syringe. The reaction mixture was stirred at 100 °C for 2 hours. Reaction control by gas chromatography showed that methyl homogeranate was completely converted. The reaction mixture was cooled to room temperature and quenched with saturated Na2CO3 solution (250 mL). The organic layer was separated from the aqueous layer, and the aqueous layer was extracted twice with 100 mL of methyl-tert-butyl ether (MTBE). The combined organic phases were dried over Na2SO4, filtered, and the solvent was removed by rotary evaporator under vacuum (100 - 10 mbar) at 40 - 50 °C. After removal of the solvent, 52 g of a yellowish residue was obtained, and the following product distribution was obtained by GC: 36.3% methyl α-cyclohomogeranate (α-1), 35.7% methyl β-cyclohomogeranate (β-1), 2.9% methyl γ-cyclohomogeranate (γ-1).

[0212] 44 g of the crude product was purified by fractional batch distillation (concentric tube column, 60 theoretical plates) at a pressure of 1 mbar, a sample temperature of 90 °C - 112 °C, and a reflux ratio of 50:1. The content and purity of the various fractions are summarized in Table 1.

[0213]

Table 1

[0214] Using the distilled fractions, fragrance samples in Table 2 were obtained.

[0215]

Table 2

[0216] Example 2: Preparation of Ethyl α-Cyclohomogeranate (α-2), Ethyl β-Cyclohomogeranate (β-2), and Ethyl γ-Cyclohomogeranate (γ-2)

Chem.

[0217] 114 g of the crude product was purified by fractional batch distillation (concentric tube column, 60 theoretical plates) at a pressure of 1 mbar, a sample temperature of 90 - 93 °C, and a reflux ratio of 50:1. The content and purity of the various fractions are summarized in Table 3.

[0218]

Table 3

[0219] Analysis by NMR showed only slight separation of the isomers. Therefore, the following fractions were combined into three fragrance samples - see Table 4. NMR-analysis of FR.4 - 8.

[0220] Ethyl α / β-cyclohomogeranate (α / β-2) The NMR data of the distillation fraction FR.4-8 showed a ratio of α-2:β-2 = 45:55. 13 C NMR (CDCl3, 126 MHz) δ (ppm) 174.4, 172.8, 135.2, 131.3, 130.5, 121.35, 60.4, 60.3, 45.6, 39.3, 35.9, 34.7, 33.8, 32.7, 32.2, 31.3, 28.1, 27.9, 26.9, 26.2, 22.9, 22.7, 20.3, 19.4, 14.2, 14.2.

[0221]

Table 4

[0222] Example 3: Preparation of methyl α-cyclohomogeranate (α-1), methyl β-cyclohomogeranate (β-1), and methyl γ-cyclohomogeranate (γ-1). A 100 mL round-bottom flask was charged with (E / Z)-methyl homogeranate (3.92 g, 20 mmol) and a PTFE-coated magnetic stir bar. The starting material was dissolved in hexafluoroisopropanol (20 mL, 9.5 equiv, 1 M), and trifluoroacetic acid (TFA, 2.38 g, 20.9 mmol) was added dropwise to the stirred solution (an immediate color change from colorless to light yellow, then to bright orange to deep orange-red was observed within 1 minute upon addition of TFA). The resulting red solution was stirred at 25 °C for 24 h. After the elapsed time, the dark brown to red reaction mixture was concentrated under reduced pressure. The residue was dissolved in hexane / MTBE (19:1 v / v, 20 mL), celite was added, and the slurry was concentrated under reduced pressure. Purification by flash column chromatography on silica gel (Merck, 40 - 63 μm, 300 g, d×l = 6×22 cm) using hexane / MTBE (gradient elution: hexane / MTBE = 19:1 - 4:1 v / v) as the eluent, followed by drying overnight in vacuo, afforded methyl cyclohomogeranate as a colorless oil (2.34 g, 11.9 mmol, 60% yield, α-1:β-1:γ-1 = 31:68:1 based on GC). The purified mixture of isomers was used as the fragrance sample (Table 5).

[0223] [Table 5]

[0224] Example 4: Preparation of Methyl γ-Cyclohomogeranate (γ-1) [Chemical formula] Under argon, a 50 mL Schlenk tube equipped with a PTFE-coated magnetic stir bar was charged with methyltriphenylphosphonium bromide (3.60 g, 10.1 mmol) and potassium tert-butoxide (1.1 g, 9.80 mmol). Anhydrous THF (25 mL) was added, and the Schlenk tube was immersed in an oil bath preheated to 50 °C, and the resulting bright yellow suspension was heated at this temperature for 2 hours. After this time, the yellow reaction mixture was cooled to 0 °C, and a solution of methyl 2-(2,2-dimethyl-6-oxocyclohexyl)acetate (0.98 g, 4.97 mmol) in dry THF (7 mL) was added dropwise. After the addition was complete, the resulting orange-brown reaction mixture was stirred at room temperature for 2.5 hours. After this time, the reaction mixture was treated with water (50 mL) and brine (50 mL), and the aqueous phase was extracted with diethyl ether (3 × 50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product as a yellow oil. Purification by flash column chromatography on silica gel using hexane / MTBE (gradient elution: hexane / MTBE 39:1 to 19:1 v / v) as the eluent gave (±)-methyl γ-cyclohomogeranate (γ-1), 753 mg, 3.84 mmol, 77% yield) as a colorless oil.

[0225] Methyl γ-cyclohomogeranate (γ-1) 1 H NMR (CDCl3, 501 MHz) δ (ppm) = 4.75 (q, J = 1.4 Hz, 1H), 4.56 (s, 1H), 3.64 (s, 3H), 2.50 (t, J = 10.2 Hz, 1H), 2.46 - 2.38 (m, 2H), 2.22 (dt, J = 12.7, 6.1 Hz, 1H), 2.05 (ddd, J = 13.1, 8.2, 5.3 Hz, 1H), 1.43 (ddd, J = 11.6, 7.2, 4.3 Hz, 1H), 1.35 (ddd, J = 13.3, 8.1, 4.9 Hz, 1H), 0.96 (s, 3H), 0.79 (s, 3H). GC DB-Waxetr 0.25 mm / 0.25 mm, 30 m, temperature: 220 °C (injector) / 2 °C / min from 60 °C to 135 °C, then 6 °C / min to 220 °C, then 12 °C / min to 260 °C, then 5 min at 260 °C, 350 °C (detector), gas: 0.60 bar H2, sample size: 0.2 μL, t R = 29.71 min (99%).

[0226] The aroma impression of the methyl γ-cyclohomogeranate (γ-1) thus obtained was evaluated. This was named sample S8.

[0227] Example 5: Preparation of methyl β-cyclohomogeranate (β-1)

Chemical formula

[0228] Methyl β-cyclohomogeranate (β-1) 1 1H NMR (CDCl3, 501 MHz) δ (ppm) = 3.66 (s, 3H), 3.05 (s, 2H), 2.01 - 1.96 (m, 2H), 1.65 - 1.54 (m, 2H), 1.58 (s, 3H), 1.48 - 1.44 (m, 2H), 0.96 (s, 6H). 13 13C NMR (CDCl3, 126 MHz) δ (ppm) = 173.5, 131.6, 130.5, 51.8, 39.5, 34.9, 33.7, 32.8, 28.1, 20.4, 19.5. GC DB-Waxetr 0.25 mm / 0.25 mm, 30 m, temperature: 220 °C (injector) / 2 °C / min from 60 °C to 135 °C, then 6 °C / min to 220 °C, then 12 °C / min to 260 °C, then 5 min at 260 °C, 350 °C (detector), gas: 0.60 bar H2, sample size: 0.2 μL, t R = 29.0 min (GC-MS: m / z [M] + = 196). HRMS (GC-EI) m / z C 12 H 20 O2 + [M] + Calculated for: 196.1458; found: 196.1457.

[0229] The aroma impression of the methyl β-cyclohomogeranate (β-1) thus obtained was evaluated. This was named Sample S10.

[0230] Example 6: Preparation of methyl (E)-2-(2,2,6-trimethylcyclohexylidene)acetate (compound of formula (IV))

Chemical formula

[0231] Methyl (E)-2-(2,2,6-trimethylcyclohexylidene)acetate (3) 1 H NMR (CD2Cl2, 501 MHz) δ (ppm) = 5.75 (s, 1H), 4.02 - 3.89 (m, 1H), 3.64 (s, 3H), 1.82 (qt, J = 12.7, 3.5 Hz, 1H), 1.62 - 1.50 (m, 3H), 1.49 - 1.42 (m, 1H), 1.39 (td, J = 12.8, 4.1 Hz, 1H), 1.22 (d, J = 7.5 Hz, 3H), 1.16 (s, 3H), 1.11 (s, 3H). 13 C NMR (CDCl3, 126 MHz) δ (ppm) = 176.2, 77.1, 52.2, 40.1, 38.0, 37.8, 32.5, 31.9, 26.1, 22.2, 21.6, 16.2. HRMS (GC-EI) m / z C 12 H 20 O2 + [M] + Calculated for: 196.1458; Found: 196.1458. GC DB-Waxetr 0.25 mm / 0.25 mm, 30 m, temperature: 220 °C (injector) / 2 °C / min from 60 °C to 135 °C, then 6 °C / min to 220 °C, then 12 °C / min to 260 °C, then 5 min at 260 °C, 350 °C (detector), gas: 0.60 bar H2, sample size: 0.2 μL, t R = 31.63 min (99%; GC-MS: m / z + = 196).

[0232] The aroma impression of methyl (E)-2-(2,2,6-trimethylcyclohexylidene) acetate (3) thus obtained was evaluated. This was named sample S11.

[0233] Example 8: Preparation of allyl 2-(2,2,6-trimethylcyclohex-2-en-1-yl) acetate (α / β-5) [Chemical formula] A 20 mL headspace Biotage microwave reactor vial was charged with a PTFE-coated magnetic stir bar and anhydrous K2CO3 (256 mg, 1.85 mmol, 1.25 eq). The vial was sealed with a rubber septum, evacuated, flame-dried, cooled to room temperature, and then refilled with argon. Carboxylic acid (a mixture of isomers α:β = 57:43; 270 mg, 1.48 mmol, 1.0 eq) and dry acetone (7.5 mL) were added in sequence. Allyl bromide (224 mg, 1.85 mmol, 1.25 eq) was transferred to the stirred colorless suspension. The rubber septum was replaced with a crimp cap equipped with a PTFE-silicone septum and sealed. The reaction vessel was immersed in an oil bath preheated to 70 °C, and the resulting colorless suspension was vigorously stirred at this temperature for 90 minutes (1400 rpm). After cooling to room temperature, the vial was opened, the colorless reaction mixture was diluted with MTBE (5 mL), and filtered through cotton wool on celite (the reaction vial was rinsed with 4 × 5 mL MTBE). The suspension was concentrated under reduced pressure and purified directly by flash column chromatography on silica gel (50 g, d×l = 3×15 cm) using hexane / MTBE (19:1 v / v) as the eluent to obtain the desired product as a colorless oil (288 mg, 1.30 mmol, 88% yield, 99% GC purity, α-5:β-5 = 55:45).

[0234] Characteristic data of individual isomers: α-5: 1 H NMR (501 MHz, CDCl3) δ (ppm) = 5.93 (ddt, J = 17.3, 10.4, 5.8 Hz, 1H), 5.36 - 5.33 (m, 1H), 5.33 (dq, J = 17.0, 1.5 Hz, 1H), 5.24 (dq, J = 10.3, 1.3 Hz, 1H), 4.58 (dt, J = 6.0, 1.3 Hz, 2H), 2.38 (dd, J = 17.4, 8.2 Hz, 1H), 2.27 - 2.19 (m, 2H), 2.01 - 1.92 (m, 2H), 1.66 (q, J = 1.9 Hz, 3H), 1.42 - 1.32 (m, 1H), 1.23 - 1.14 (m, 1H), 0.92 (s, 3H), 0.84 (s, 3H). 1313C NMR (126 MHz, CDCl3) δ (ppm) = 174.2, 135.3, 132.4, 121.6, 118.4, 65.3, 45.7, 35.9, 32.4, 31.5, 27.0, 26.4, 23.0, 22.9.

[0235] β-5: 1 1H NMR (501 MHz, CDCl3) δ (ppm) = 5.92 (ddt, J = 17.2, 10.4, 5.7 Hz, 1H), 5.32 (dq, J = 17.2, 1.6 Hz, 1H), 5.22 (dq, J = 10.4, 1.4 Hz, 1H), 4.57 (dt, J = 5.7, 1.4 Hz, 2H), 3.08 (s, 2H), 1.99 (t, J = 6.4 Hz, 2H), 1.63 - 1.56 (m, 2H), 1.59 (s, 3H), 1.48 - 1.44 (m, 2H), 0.96 (s, 6H). 13 13C NMR (126 MHz, CDCl3): δ (ppm) 172.6, 132.6, 131.7, 130.5, 118.1, 65.2, 39.5, 34.9, 33.9, 32.9, 28.1, 20.5, 19.5. GC DB - 1 0.25 mm / 0.25 mm, 30 m, temperature: 220 °C (injector) / 2 °C / min from 50 °C to 140 °C, then 12 °C / min to 350 °C, 350 °C (detector), gas: 0.60 bar H2, split ratio 120:1, sample size: 0.2 μL; t R (α - isomer) = 41.0 min (54%; GC - MS: m / z [M] + = 222), t R (β - isomer) = 41.3 min (44%; GC - MS: m / z [M] + = 222); 99% GC purity. HRMS (GC - EI) m / z C 14 H 22 O2 + [M] + Calculated value for: 222.1614; Measured value: 222.1614.

[0236] The allyl 2-(2,2,6-trimethylcyclohex-2-en-1-yl) acetate (α / β-5) thus obtained was evaluated for its aroma impression. This was named Sample S12.

[0237] Example 9: Preparation of (±)-methyl 1-hydroxy-2,2,6-trimethylcyclohexaneacetate (4) [Chemical formula] The newly distilled diisopropylamine (1.59 g, 15.7 mmol, 1.7 eq) was transferred under argon to a flame-dried two-necked round-bottom flask equipped with a rubber septum and an argon outlet. Dry THF (15 mL) was added, and the flask was immersed in a dry ice / acetone cooling bath at -78 °C. After 10 minutes, n-butyllithium (2.5 M solution in n-hexane, 4.30 g, 15.5 mmol, 1.7 eq) was added dropwise, and the resulting yellow solution was stirred at this temperature for 15 minutes. Then, anhydrous methyl acetate (1.02 g, 13.8 mmol, 1.5 eq) was added dropwise, and stirring was continued at -78 °C for an additional 30 minutes. Next, a solution of commercially available 2,2,6-trimethylcyclohexan-1-one (1.29 g, 9.21 mmol, 1.0 eq) in THF (10 mL) was added, and the reaction mixture was stirred at -78 °C for an additional 2 hours. After the elapsed time, saturated aqueous ammonium chloride solution (20 mL) was added, followed by water (20 mL) and MTBE (20 mL). The organic phase was separated, and the aqueous phase was extracted with MTBE (3 × 20 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product as a pale yellow oil as a mixture of diastereomers. Purification by flash column chromatography on silica gel (gradient elution: hexane / MTBE = 39:1 to 19:1 v / v) gave, in addition to a mixed fraction (863 mg, 4.03 mmol, 44% yield) of 4:epi-4 = 2.7:1, the diastereomerically pure equatorial isomer 4 (912 mg, 4.26 mmol, 46% yield) as a colorless oil. This corresponds to a yield of 78% for 4 and 12% for epi-4, giving an overall yield of 90%. The 4 thus obtained was evaluated for its aromatic impression. This was named sample S13.

[0238] Characteristic data of the major diastereomer 4:

Chemical formula

[0239] Regarding minor diastereomer epi - 4 1 H and 13 13C NMR data:

Chemical Structure

[0240] 3. Olfactory Impression To test the quality and strength of the compounds and mixtures of the present invention, a scent strip test was conducted.

[0241] For this purpose, strips of absorbent paper were immersed in a solution containing 1 - 10% by weight of the test compound in triethyl citrate. After the solvent was evaporated (about 30 seconds), a trained perfumer evaluated the scent impression by smell.

[0242] The aroma impressions of the mixtures prepared according to the present invention, including the compounds of formula (Ia) and formula (Ib), are shown in Table I below. This compound was formulated in a perfume composition according to Tables II and III and designated as Compound A.

[0243] Compounds according to the compounds of formula (Ia), (Ib), and (Ic) are:[[]]

Chemical formula

[0244]

Table 6

[0245] 4. Advantageous Compositions The mixtures / compounds shown in Table I were formulated as compositions according to Tables II and III. The mixtures shown in Table I were designated as "Compound A" in Tables II and III.

[0246]

Table 7

[0247]

Table 8

[0248] The compositions according to Tables II and III, namely 1A, 1B, 2A, and 2B, can be included in various compositions selected from the group consisting of deo pump spray, clean hair conditioner, face wash gel, foam bath concentrate, hair gel, self-foaming body wash, sprayable sun care emulsion, sprayable sun protection emulsion, emollient facial gel, two-phase oil foam bath, shampoo, shower bath, hydroalcoholic AP / deo pump spray, aerosol, aqueous / alcoholic AP / deo roll-on, styling gel type "Out of Bed", shaving foam, baby shampoo for sensitive skin, body wash for sensitive skin, gloss enhancing shampoo for sensitive scalp, deo stick, baby wipe, aftershave balm, face gel, face day care cream, face cleanser, body lotion, sun care SPF50+, sprayable lotion, hand dish cleaner - regular, hand dish cleaner - concentrate, sanitizing detergent - concentrate, multi-purpose cleaner, antibacterial softener, detergent composition, powder detergent composition, and liquid detergent composition.

[0249] Those skilled in the art will be familiar with the various common formulations in the above-mentioned products.

[0250] Compositions 1A, 1B, 2A, and 2B can be formulated in a specific formulation as disclosed, for example, in IP.com number: IPCOM000258614D, title New Aroma Chemicals, pages 6 - 46, Tables 1 - D13, in which case "Fragrance Composition 1A" is replaced with the same amount of Composition 1A, 1B, 2A, or 2B.

Claims

1. At least one compound of formula (I) for imparting an aromatic impression to a composition 【Chemistry 1】 or its stereoisomer (In the formula, X １ and X ３ They come together and form a double bond between the carbon atoms they are bonded to, X ２ and X ４ It is provided that it is hydrogen; or X ３ and X ４ They come together and form a double bond between the carbon atoms they are bonded to, X １ and X ２ It is provided that it is hydrogen; or X ２ and X ３ together form a double bond between the carbon atoms to which they are attached, provided that X １ and X ４ are hydrogen; or X ４ OH and X １ , X ２ , and X ３ It is all hydrogen, R is C １ ~C ５ Linear or branched alkyl and C ３ ~C ５ (Selected from linear or branched alkenyls) Use.

2. The compound of formula (I) at least one compound of formula (Ia) 【Chemistry 2】 or its stereoisomer or mixture thereof or at least one compound of formula (Ib) 【Transformation 3】 or at least one compound of formula (Ic) 【Chemistry 4】 or its stereoisomer or mixture thereof or at least one compound of formula (Id) 【Transformation 5】 or its stereoisomer or mixture thereof or mixtures thereof (In the formula, R is C １ ~C ５ Linear or branched alkyl and C ３ ~C ５ The use according to claim 1, comprising (selected from linear or branched alkenyls).

3. The use according to claim 1, wherein R is selected from methyl, ethyl, propyl, butyl, isobutyl, isopropyl, 1-propenyl, or 2-propenyl.

4. The use according to claim 1, wherein R is selected from methyl, ethyl, or 1-propenyl.

5. Use of the mixture according to claim 2, wherein the weight ratio of at least one compound of formula (Ia) and at least one compound of formula (Ib) is in the range of 0.1:99.9 to 99.9:0.

1.

6. Use of the mixture according to claim 2, wherein the weight ratio of at least one compound of formula (Ia) and at least one compound of formula (Ib) is in the range of 40:60 to 60:

40.

7. The use of the mixture according to claim 2, wherein the mixture has a ratio in the range of 90:10 to 99.9:0.1, where the ratio represents the total amount of the compound of formula (Ia) and the compound of formula (Ib) relative to the compound of formula (Ic).

8. A method for imparting an aromatic note to a composition, comprising at least the step of adding a compound of formula (I) according to any one of claims 1 to 7 to the composition.

9. The use or method according to claim 1, wherein the aforementioned aromatic impression is selected from the group consisting of woody notes, fruity notes, herbal notes, green notes, rooty notes, citrus notes, petitgrain notes, floral notes, damascon notes, tobacco notes, ashtray notes, gourmet notes, sweet notes, vetiver notes, ionone notes, ambra notes, fresh notes, natural notes, fur needle notes, camphor-like notes, or any combination of two or more of these.

10. The use or method according to claim 1, wherein at least one compound of formula (I) is used in a total amount ranging from 0.001% by weight or more to 70.0% by weight or less, based on the total weight of the composition.

11. i) At least one compound of formula (I) as described in any one of claims 1 to 7, ii) At least one aromatic chemical substance (X) different from the compound of formula (I), or iii) At least one non-aromatic chemical carrier, or A composition comprising both (iv) (ii) and (iii).

12. The composition according to claim 11, wherein at least one compound according to any one of claims 1 to 7 is present in an amount ranging from 0.01% by weight or more to 70.0% by weight or less, based on the total weight of the composition.

13. The composition according to claim 11, wherein the at least one non-aromatic chemical carrier (ii) is selected from a surfactant, an oil component, an antioxidant, a deodorizing agent, or a solvent.

14. The composition according to claim 11, wherein the composition is selected from perfume compositions, body care compositions, sanitary products, cleaning compositions, textile detergent compositions, fragrance dispenser compositions, food products, nutritional supplements, pharmaceutical compositions, or crop protection compositions.

15. at least one compound of formula (Ib) 【Transformation 6】 or its stereoisomer or a mixture thereof, at least one compound of formula (IV) 【Transformation 7】 or its stereoisomer or mixture thereof (In the formula, R is C １ ~C ５ Linear or branched alkyl and C ３ ~C ５ A mixture comprising (selected from linear or branched alkenyls).

16. A method for preparing a mixture of at least one compound of formula (I) according to any one of claims 1 to 7, a) Using a catalytic amount of acid, the compound of formula (III) 【Transformation 8】 (In the formula, R is C １ ~C ５ Linear or branched alkyl and C ３ ~C ５ (Selected from linear or branched alkenyls) A step of cyclizing to produce at least one compound of formula (I), b) A method comprising at least the step of optionally purifying at least one compound of formula (I).

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