Esters and ethers of 5-isopropyl-2-methylcyclohex-1-ol as perfume ingredients

Abstract

The present invention relates to the use of a compound of formula (I) or a mixture thereof with a compound of formula (II), in which R and dashed lines are as defined in the claims and description, as an aroma ingredient, to the use thereof to impart aroma to a composition, and to a method for imparting aroma to a composition. The invention further relates to a composition comprising a compound of formula (I) or a mixture thereof with compound (II), to a mixture of a compound of formula (I) with compound (II), and to a specific compound of formula (I). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the use of esters and ethers of 5-isopropyl-2-methylcyclohexan-1-ol of formula (I) as defined below and mixtures thereof with compounds of formula (II) as defined below as fragrance components, or for imparting fragrance to a composition, or for enhancing and / or modifying the fragrance of a composition. The present invention further relates to a composition comprising a compound of formula (I) or a mixture of a compound of formula (I) and a compound of formula (II), to a mixture of a compound of formula (I) and compound (II), and to specific compounds of formula (I). Background Art

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

[0003] Although a large number of synthetic aroma chemicals already exist, there is a continuing need for new components in order to meet the numerous properties desired in the extremely diverse fields of application. These include above all sensory properties, i.e. the compounds should have favorable odor (olfactory) properties. In addition, aroma chemicals should also have additional positive secondary properties such as an efficient preparation method, the potential to provide better sensory properties due to synergistic effects with other aroma chemicals, higher stability under certain application conditions, and / or higher substantivity.

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

[0005] Particularly interesting are aroma chemicals which can impart one or more different sensory effects to a composition, thus contributing to the rich and interesting sensory properties of the composition, especially olfactory properties. In this regard, aroma chemicals which can impart fresh, minty, musty, carrot-like, natural, rooty, violet, powdery, floral, woody, warm, ionone, fruity, camphoraceous, citrus, herbal, etheric, gourmand, anise, ambrettolide-like, animalic, civet, soft, incense, musty, fatty, tobacco, green, spicy, acidulous, juniper, pepper, menthol, cedar, dandelion, earthy, food-like notes or any combination of two or more of these notes are of primary interest. In addition, substantivity and persistence are of particular interest in order to obtain a long-lasting odor effect in the composition and on the surface treated with the composition.

[0006] However, since even minor changes in chemical structure can cause significant changes in sensory properties such as odor and / or flavor, it is extremely difficult to target the search for substances with certain and distinct sensory properties such as a certain odor. Thus, in most cases, the search for new aroma chemicals is difficult and laborious without knowing whether a substance with the desired odor and / or flavor will actually be found.

[0007] The object of the present invention is to provide substances that can be used as aroma chemicals either alone or as a mixture in a composition; in particular, to seek substances with enhanced odor with a pleasant smell. Furthermore, they should be combinable with other aroma chemicals, thus allowing the generation of novel and advantageous sensory properties and being usable in a composition.

[0008] The object of the present invention is to provide a new aroma chemical or mixture of aroma chemicals that has a pleasant aroma, in particular a pleasant olfactory effect; preferably a combination of one or two or more of the effects selected from the following groups: fresh note, minty note, stale note, carrot-like note, natural note, rooty note, violet note, powdery note, floral note, woody note, warm note, ionone note, fruity note, camphor note, citrus note, herbal note, etheric note, gourmand note, anise note, ambroxan-like note, animalic note, civet note, soft note, incense note, musty note, fatty note, tobacco note, green note, spicy note, acid fruity note, turpentine note, pepper note, spearmint note, cedarwood note, dandelion note, earthy note, food-like note.

[0009] A further object of the present invention is that the aroma chemical should be obtainable from readily available starting materials, thus allowing its rapid and economical manufacture.

[0010] This is of particular interest when the aroma chemical is used in compositions such as care compositions, hygiene products, cleaning compositions, textile detergent compositions, and compositions for aroma dispensers. Summary of the Invention

[0011] These objects are achieved by providing compounds of formula (I) and mixtures thereof with a compound (II). It has surprisingly been found that the compounds of formula (I) and mixtures thereof according to the invention have an agreeable olfactory effect; wherein certain compounds (I) or certain mixtures of a compound (I) with a compound (II) (as described below) exhibit an effect selected from the following, preferably a combination of two or more effects: fresh note, minty note, stale note, carrot-like note, natural note, rooty note, violet note, powdery note, floral note, woody note, warm note, ionone note, fruity note, camphoraceous note, citrus note, herbal note, etheric note, gourmand note, anise note, ambrettolide-like note, animalic note, civet note, soft note, incense note, musty note, fatty note, tobacco note, green note, spicy note, acidic fruity note, turpentine note, pepper note, spearmint note, cedarwood note, dandelion note, earthy note, food-like note.

[0012] Accordingly, a first aspect of the invention relates to at least one compound of formula (I)

[0013]

[0014] or a stereoisomer thereof or a mixture of different stereoisomers,

[0015] wherein

[0016] ---- (i.e., the interrupted bond / dashed line) represents a single bond or a double bond, and

[0017] R is a straight-chain or branched C1-C6-alkyl, formyl, or a straight-chain or branched C1-C4-alkylcarbonyl,

[0018] or a mixture of a compound of formula (I) with a compound of formula (II) as defined below

[0019] for use as an aroma chemical.

[0020] Another aspect of the invention relates to the use of a compound of formula (I) or a mixture of a compound (I) with a compound (II) as defined below for imparting an aromatic effect to a composition.

[0021] Another aspect of the invention relates to the use of a compound of formula (I) or a mixture of a compound (I) and a compound (II) as defined below for enhancing and / or modifying the aromatic character of a composition.

[0022] Another aspect of the present invention relates to a method for imparting an aromatic effect to a composition, which method comprises at least the following steps: adding a compound of formula (I) or a mixture of the aforementioned (I) and (II) to the composition to be aromatized, or mixing at least one compound of formula (I) or a mixture of the aforementioned (I) and (II) simultaneously or continuously with other components of the composition, or mixing at least one compound of formula (I) or a mixture of the aforementioned (I) and (II) with a preformed mixture of a part of the other components of the composition.

[0023] Another aspect of the present invention relates to a method for enhancing the aroma of a composition. The method comprises the following steps: adding at least one compound of formula (I) or a mixture of the aforementioned (I) and (II) to the composition whose aroma is to be enhanced, or mixing at least one compound of formula (I) as defined above or a mixture of the aforementioned (I) and (II) simultaneously or continuously with other ingredients of the composition, such as at least one other aroma chemical different from the compounds of formula (I) and (II) and / or at least one non-aromatic chemical carrier, or mixing at least one compound of formula (I) as defined above or a mixture of the aforementioned (I) and (II) with a preformed mixture of a part of the other components of the composition in order to obtain an aromatic composition.

[0024] Yet another aspect of the present invention relates to a method for intensifying and / or altering the aroma of a composition. The method comprises the following steps: incorporating at least one compound of formula (I) or the aforementioned mixture into an aromatic composition in order to obtain an aromatic composition with an altered aroma, for example by taking the steps mentioned above for other methods of the present invention.

[0025] Another aspect of the present invention relates to a mixture which comprises at least one compound of formula (I)

[0026]

[0027] or a stereoisomer thereof or a mixture of different stereoisomers,

[0028] wherein

[0029] ---- represents a single bond or a double bond, and

[0030] R is a straight-chain or branched C1-C6-alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl;

[0031] and

[0032] at least one compound of formula (II)

[0033]

[0034] or a stereoisomer thereof or a mixture of different stereoisomers

[0035] wherein

[0036] R is a straight-chain or branched C1-C6-alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl.

[0037] Another aspect relates to a composition comprising at least one compound of formula (I) as defined above or a mixture of at least one compound of formula (I) and at least one compound of formula (II) as defined above, and

[0038] i. at least one aroma chemical (X) different from the compounds of formula (I) and (II), or

[0039] ii at least one non-aromatic chemical carrier, or

[0040] iii both (i) and (ii).

[0041] Another aspect of the invention relates to a compound (Ia)

[0042]

[0043] or a stereoisomer thereof or a mixture of different stereoisomers

[0044] wherein R is isopropylcarbonyl.

[0045] Another aspect of the invention relates to a compound of formula (Ib)

[0046]

[0047] or a stereoisomer thereof or a mixture of different stereoisomers

[0048] wherein

[0049] R is a straight-chain or branched C1-C6-alkyl; wherein R is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl, wherein more preferably R is methyl or ethyl, and in particular ethyl.

[0050] Furthermore, the compounds of formula (I), the compounds of formula (II), or mixtures thereof can be produced in good yield and purity by a simple synthesis starting from readily available starting materials, and can be produced on a large scale and in a simple and cost-effective manner. Detailed Description

[0051] References throughout this specification to "one embodiment" or "an embodiment" or "a preferred embodiment" mean that a particular feature, structure, or property described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, the appearances of the phrases "in one embodiment" or "in a preferred embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, but may refer to the same embodiment. Furthermore, in one or more embodiments, as will be apparent to those skilled in the art from this disclosure, the features, structures, or properties may be combined in any suitable manner. Additionally, although some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the subject matter, and form different embodiments, as will be understood by those skilled in the art. For example, in the appended claims, any of the claimed embodiments can be used in any combination.

[0052] Furthermore, ranges defined throughout this specification also include the end values, i.e., a range of 1 to 10 means that both 1 and 10 are included within the range. To avoid doubt, the applicant reserves the right to obtain any equivalent means under applicable law.

[0053] In the context of the present invention, the term "aromatic" refers to a sensory property and includes odor and / or flavor. Sensory properties are related to human sensory perception.

[0054] The term "aromatic chemical" denotes a substance used to obtain a sensory or organoleptic (used interchangeably herein) effect and includes its use for obtaining an olfactory and / or flavor effect. The term "olfactory effect" or "olfactory note" (used interchangeably herein) denotes an odor effect without any positive or negative judgment, while the term "aroma effect" or "fragrance effect" (used interchangeably herein) as used herein relates to an odor effect that is generally perceived as pleasant. Thus, "fragrance" or "aroma" denotes an aromatic chemical that mainly causes a pleasant odor effect. Flavor denotes an aromatic chemical that causes a taste effect.

[0055] As used herein, the term "aromatic composition" refers to a composition that causes or has an aroma. The term aromatic composition includes "odor composition" and / or "flavor composition". An odor composition is a composition that mainly causes an odor effect, and a flavor composition is a composition that mainly causes a taste effect.

[0056] The term "aromatic property" denotes the overall aromatic effect of an aromatic chemical and is constituted by the individual aromatic effects of the aromatic chemical.

[0057] The term odor composition includes "fragrance composition" or "aroma composition" (used interchangeably herein), where the "fragrance composition" or "aroma composition" mainly causes an odor effect that is generally perceived as pleasant.

[0058] The general expressions "favorable sensory properties" or "advantageous sensory properties" describe the pleasantness and clarity of the sensory effects conveyed by aroma chemicals. "Pleasantness" and "clarity" are terms familiar to those skilled in the art, such as perfumers. Pleasantness generally refers to a spontaneously induced, positively perceived, agreeable sensory effect. However, "pleasant" is not necessarily synonymous with "sweet". "Pleasant" can also be the odor of musk or sandalwood. "Clarity" generally refers to a spontaneously induced sensory effect that, for the same test panel, reproducibly evokes the same specific thing. For example, a substance can have an odor that spontaneously evokes "apple": the odor will then clearly be "apple". If the apple odor is very agreeable because it evokes, for example, a sweet, fully ripe apple, then the odor will be called "pleasant". However, the odor of a typical sour apple can also be clear. If two reactions occur after smelling the substance, in this instance thus a pleasant and clear apple odor, then the substance has particularly favorable sensory properties.

[0059] When the expressions "combination of...", "in combination with...", or "combined with..." are used herein to refer to a composition, method, or use of two compounds, it is taken into account that the two compounds need not be used in the form of a physical mixture of the said compounds, but can be used separately (e.g., added). When the compounds are used separately, they can be used (e.g., added) in any order, successively (i.e., one after another) or simultaneously (i.e., substantially at the same time).

[0060] The term "boosting" or "boost" is used herein to describe the action of enhancing and / or altering the aroma of an aroma chemical or composition (correspondingly an aromatic composition). The term "enhancing" includes an improvement in the pleasantness and / or clarity of the aroma and / or an improvement in intensity. The term "altering" includes a change in the aroma attributes. The terms "pleasantness" and "clarity" are familiar to those skilled in the art, such as perfumers, and have the corresponding meanings.

[0061] Intensity can be determined via threshold determination. The threshold of an odor is the concentration of the substance in the relevant gas space at which the odor effect can just still be perceived by a representative test panel, although no longer necessary for defining the odor effect.

[0062] When an application characterized by a top note is desired, where the odor is to be conveyed particularly quickly and strongly, a boosting action is particularly desired in the fragrance composition, for example in deodorants, air fresheners, or in the flavoring part of chewing gum.

[0063] The terms "the invention relates to" and "the invention is directed to" are used synonymously throughout this invention.

[0064] The term "persistence" describes the evaporation behavior of fragrance chemicals over time. Persistence can be determined, for example, by applying a fragrance chemical to a test strip and subsequently performing an olfactory evaluation of the odor effect of the test strip. For fragrance chemicals with high persistence, the panel can still identify a long time span of the fragrance effect.

[0065] The term "fastness" describes the interaction of a fragrance chemical with a surface (such as skin or textiles), especially after subsequent treatment of the surface (such as washing). Fastness can be determined, for example, by washing a textile with a textile detergent composition containing the fragrance chemical and subsequently performing an olfactory evaluation of the textile (wet textile) directly after washing and of the dry textile after long-term storage.

[0066] The term "stability" describes the behavior of a fragrance chemical after contact with oxygen, light, and / or other substances. A fragrance chemical with high stability retains its fragrance properties over a long period of time, preferably in various compositions and under various storage conditions.

[0067] In order to impart a persistent fragrance effect to a composition or to a surface treated with a composition, the persistence, fastness, and stability of the fragrance chemical in the composition should preferably be high.

[0068] As used herein, the term "compound (I)" or "compounds (I)" refers to one or more compounds having formula (I), including all stereoisomeric forms (stereoisomers) thereof in all ratios and their salts. The terms "compound (I)" or "compound having formula (I)" or simply "(I)" are used interchangeably. This also applies to compounds having formula (II).

[0069] The term "stereoisomers" is a general term for all isomers of individual compounds that differ only in the orientation of their atoms in space and not in the connectivity of the atoms. Thus, the term stereoisomers includes mirror-image isomers (enantiomers), geometric (cis / trans or E / Z) isomers, and diastereoisomers. For precise definitions of these terms, see G. Helmchen in Houben-Weyl E21a, Stereoselective Synthesis [Stereoselective Synthesis], G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds.), 1995, 1-74: "Vocabulary and Nomenclature of Organic Stereochemistry [Vocabulary and Nomenclature of Organic Stereochemistry]". The possible isomers can exist as mixtures (i.e., racemates, cis / trans-mixtures or mixtures of diastereoisomers).

[0070] In the present case, compound (I) in which the dashed line (----) is a single bond has at least three stereocenters, namely the carbon ring atoms carrying a methyl group, an isopropyl group, and an -OR group. Compound (I) in which the dashed line is a double bond has at least two stereocenters, namely the carbon ring atoms carrying a methyl group and an -OR group. In addition, if R is or contains a branched C4-C6 alkyl group, R can also contain one or more stereocenters (such as, for example, in sec-butyl).

[0071] For the purposes of the present invention, the term "pure enantiomer" is understood to mean a non-racemic mixture of a specific compound in which the desired enantiomer is present in an enantiomeric excess of >90% ee.

[0072] For the purposes of the present invention, the term "pure diastereoisomer" is understood to mean a mixture of diastereoisomers of a specific compound in which the desired diastereoisomer is present in an amount of >90% based on the total amount of the diastereoisomers of said compound.

[0073] In the context of the present invention, the terms "(I)", "compound (I)" or "compound having the formula (I)", when not defined as a specific stereoisomer or a specific mixture of stereoisomers, refer to the compound as obtained in the form in which it is obtained in a non-stereoselective method for its production. However, this term is also used if it is not necessary or possible to specify the stereochemistry of compound (I) in more detail. This also applies to compound (II).

[0074] The term "alkyl" denotes in each case a straight-chain (=linear) or branched alkyl group having the specified number of carbon atoms. Examples of C1-C2-alkyl are methyl and ethyl. Examples of C1-C3-alkyl are methyl, ethyl, n-propyl and isopropyl. Examples of C1-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (=sec-butyl), isobutyl and tert-butyl. Examples of C1-C6-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (=sec-butyl), isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and its (other) structural isomers.

[0075] Formyl is the group -CH(=O).

[0076] Straight-chain or branched C1-C4-alkylcarbonyl is the group -C(=O)-R', where R' is a straight-chain or branched C1-C4-alkyl. Examples are methylcarbonyl (acetyl), ethylcarbonyl (propionyl), n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, 2-butylcarbonyl (=sec-butylcarbonyl), isobutylcarbonyl and tert-butylcarbonyl.

[0077] Use:

[0078] One embodiment of the present invention relates to at least one compound having the formula (I)

[0079]

[0080] or its stereoisomers or a mixture of its different stereoisomers,

[0081] wherein

[0082] ---- represents a single bond or a double bond, and

[0083] R is a straight-chain or branched C1-C6-alkyl, formyl, or a straight-chain or branched C1-C4-alkylcarbonyl,

[0084] for use as an aroma chemical or for imparting an aromatic effect to a composition.

[0085] In a preferred embodiment, the present invention relates to at least one compound having formula (I), wherein the compound having formula (I) is a compound having formula (Ia) (which is compound (I) wherein the dashed line (----) represents a single bond).

[0086]

[0087] or a stereoisomer thereof or a mixture of different stereoisomers,

[0088] wherein

[0089] R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group,

[0090] for use as an aroma chemical or for imparting an aromatic effect to a composition.

[0091] In another embodiment, the present invention relates to at least one compound having formula (I), wherein the compound having formula (I) is a compound having formula (Ib) (which is compound (I) wherein the dashed line (----) represents a double bond),

[0092]

[0093] or a stereoisomer thereof or a mixture of different stereoisomers,

[0094] wherein

[0095] R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group,

[0096] for use as an aroma chemical or for imparting an aromatic effect to a composition.

[0097] Among compounds (Ia) and (Ib), compound (Ia) is preferred.

[0098] In a preferred embodiment, R is a straight-chain or branched C1-C6-alkyl group, wherein the C1-C6-alkyl group is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

[0099] More preferably, R is methyl or ethyl.

[0100] In another preferred embodiment, R is a formyl group or a straight-chain or branched C1-C4-alkylcarbonyl group.

[0101] In a more preferred embodiment, R is a straight-chain or branched C1-C4-alkylcarbonyl group, wherein the C1-C4-alkylcarbonyl group is preferably selected from methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl and tert-butylcarbonyl.

[0102] More preferably, R is a C1-C3-alkylcarbonyl. Even more preferably, R is methylcarbonyl, ethylcarbonyl or isopropylcarbonyl. Particularly preferably, R is methylcarbonyl or ethylcarbonyl.

[0103] In a particularly preferred embodiment, the compound of formula (I) is a compound of formula (Ia), wherein R is a straight-chain or branched C1-C3-alkylcarbonyl, in particular methylcarbonyl, ethylcarbonyl or isopropylcarbonyl and more particularly methylcarbonyl or ethylcarbonyl.

[0104] Preferred embodiments of the present invention relate to the use of at least one compound of formula (I) as an aroma chemical for imparting the following fragrance notes: fresh fragrance note, mint fragrance note, stale fragrance note, carrot-like fragrance note, natural fragrance note, root fragrance note, violet fragrance note, powdery fragrance note, floral fragrance note, woody fragrance note, warm fragrance note, ionone fragrance note, fruity fragrance note, camphor fragrance note, citrus fragrance note, herbal fragrance note, etheric fragrance note, gourmand fragrance note, anise fragrance note, ambrettolide-like fragrance note, animalic fragrance note, civet fragrance note, soft fragrance note, incense fragrance note, musty fragrance note, fatty fragrance note, tobacco fragrance note, green leaf fragrance note, acidic fruit fragrance note, or a combination of two or more of these fragrance notes.

[0105] In an embodiment, the compound of formula (I) includes a compound of formula (Ia) and a compound of formula (Ib).

[0106] In a further embodiment, the present invention relates to the use of at least one compound of formula (I) for enhancing the aroma of a composition.

[0107] In a preferred embodiment of the present invention, the compound of formula (I) is used as a perfume or as an ingredient of a fragrance composition or for imparting fragrance to a composition.

[0108] In particular, the at least one compound of formula (I) is used for imparting to the composition a fragrance note selected from the following: fresh fragrance note, mint fragrance note, stale fragrance note, carrot-like fragrance note, natural fragrance note, root fragrance note, violet fragrance note, powdery fragrance note, floral fragrance note, woody fragrance note, warm fragrance note, ionone fragrance note, fruity fragrance note, camphor fragrance note, citrus fragrance note, herbal fragrance note, etheric fragrance note, gourmand fragrance note, anise fragrance note, ambrettolide-like fragrance note, animalic fragrance note, civet fragrance note, soft fragrance note, incense fragrance note, musty fragrance note, fatty fragrance note, tobacco fragrance note, green leaf fragrance note, acidic fruit fragrance note or a combination of two or more of these fragrance notes.

[0109] More particularly, the at least one compound of formula (I) is used to impart to the composition a combination of two or more of the following effects: fresh note, mint note, stale note, carrot-like note, natural note, rooty note, violet note, powdery note, floral note, woody note, warm note, ionone note, fruity note, camphor note, citrus note, herbal note, etheric note, gourmand note, anise note, ambroxan-like note, animalic note, civet note, soft note, incense note, musty note, fatty note, tobacco note, green note, acidulous fruity note or a combination of two or more of these notes.

[0110] Suitable compositions are, for example, compositions for personal care, household care, industrial applications and compositions for other applications such as pharmaceutical compositions or crop protection compositions.

[0111] Preferably, the compound of formula (I) according to the invention is used in compositions selected from: perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions or crop protection compositions. Further details are given below in the context of the compositions of the invention.

[0112] Compound (I) can be obtained by standard methods of organic chemistry, generally by etherification (alkylation) or esterification (acylation) of the corresponding alcohols 5-isopropyl-2-methylcyclohexan-1-ol (for the preparation of compound (Ia)) or 3-isopropyl-6-methylcyclohex-2-en-1-ol (for the preparation of compound (Ib)).

[0113] Suitable etherification and esterification conditions are known in the art.

[0114] Etherification can be carried out by reacting the alcohol with an alkylating agent R-X typically in the presence of a base, where R is a C1-C6-alkyl and X represents a leaving group, such as a halogen atom, e.g., Cl, Br or I, or a sulfonate group, e.g., tosylate, mesylate, triflate or perfluorobutanesulfonate. Suitable bases can be inorganic bases or organic bases. Suitable inorganic bases are, for example, alkali metal carbonates, such as Li2CO3, Na2CO3, K2CO3 or Cs2CO3, alkali metal hydroxides, such as LiOH, NaOH or KOH, and hydride donors, such as NaH, LiAlH4 or NaBH4. Examples of suitable organic bases are tertiary amines, such as trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine, etc., or basic N-heterocycles, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN. Particularly advantageous is NaH because the hydrogen formed in its reaction with the alcohol drives the reaction even more strongly.

[0115] The alkylation reaction is carried out under conventional alkylation reaction conditions well-known to those skilled in the art.

[0116] The reaction can be carried out in a solvent or in the pure state. Examples of suitable solvents are listed below in the context of the esterification reaction.

[0117] After completion of the reaction, the etherification product can be separated by conventional means, if necessary after neutralization (especially if X is a halogen atom or if acidic conditions are applied), e.g., by distillation, extraction or chromatography. If desired, the separated product can subsequently be further purified.

[0118] Esterification can be carried out by reacting the alcohol (i.e., 5-isopropyl-2-methylcyclohexan-1-ol for preparing compound (Ia) or 3-isopropyl-6-methylcyclohex-2-en-1-ol for preparing compound (Ib)) with the desired acid R-C(O)OH (where R is H or a C1-C4-alkyl), i.e., with one of formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid or valeric acid, or with its more reactive derivatives such as its halides (especially chlorides) or its acid anhydrides under typical esterification conditions; if necessary, by removing the reaction water formed (if using the acid itself) or the acid formed (if using the acid anhydride) to enhance the reaction rate, or by neutralization (if using an acyl halide). The reaction is usually carried out in the presence of an esterification catalyst. Suitable esterification catalysts that can be used in this reaction are well-known to those skilled in the art. Suitable esterification catalysts are, for example, metal-based catalysts, such as iron, cadmium, cobalt, lead, zinc, antimony, magnesium, titanium and tin catalysts in the form of metals, metal oxides or metal salts, such as metal alkoxides; or acids, such as inorganic acids, e.g., sulfuric acid, hydrochloric acid or phosphoric acid; organic sulfonic acids, such as methanesulfonic acid or p-toluenesulfonic acid, or acidic ion exchangers.

[0119] The reaction of acyl halides R-C(O)-X (where X is a halogen atom) with alcohols is usually carried out in the presence of a base. Suitable bases are preferably selected from organic bases. Suitable organic bases that can be used are, for example, tertiary amines such as trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine, etc., or basic N-heterocycles such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.

[0120] The reaction of acid anhydrides is usually also carried out in the presence of a base. Suitable bases are listed above. DMAP is particularly preferred here.

[0121] Alternatively, the esterification can be carried out as a Steglich esterification using coupling reagents such as N,N'-bis(prop-2-yl)methanediimine (DIC) or dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as a catalyst.

[0122] The esterification reaction can be carried out in a solvent or in the pure state. Suitable solvents are, for example, alkanes such as hexane or heptane, halogenated C1-C4-alkanes such as dichloromethane, chloroform or dichloroethane, cycloalkanes such as cyclohexane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene or dichlorobenzene, aliphatic ethers such as diisopropyl ether or methyl tert-butyl ether, cyclic ethers such as tetrahydrofuran or dioxane, etc. The specified solvents can be used alone or in the form of a mixture with another solvent.

[0123] After completion of the reaction, the esterification product can be separated by conventional means, if necessary, after neutralization (especially if acid halides or acid anhydrides are used as starting materials or if an excess of acid is used) and / or after removal of the catalyst (especially if the catalyst is a solid, such as one of the above-mentioned metal-based catalysts or ion exchange resins), for example by distillation, extraction or chromatography. If necessary, the separated product can subsequently be further purified.

[0124] The alcohol can further be obtained from commercially available 3-isopropyl-6-methylcyclohex-2-en-1-one (carvone). Its keto group can be selectively reduced to obtain 3-isopropyl-6-methylcyclohex-2-en-1-ol; alternatively, 3-isopropyl-6-methylcyclohex-2-en-1-one can be subjected to a hydrogenation reaction in which both the C-C and C-O double bonds are hydrogenated to obtain 5-isopropyl-2-methylcyclohex-1-ol. The selective reduction of the keto group (wherein the C-C double bond is not hydrogenated) can be carried out using a suitable reducing agent such as a coordination hydride, for example LiAlH4 (lithium aluminum hydride) or NaBH4. The hydrogenation reaction in which both the C-C and C-O double bonds are reduced can be carried out under conventional hydrogenation conditions, such as typically under high pressure in the presence of a hydrogenation catalyst such as a Group VIII metal, for example Pt, Pd or Ni. To prepare 5-isopropyl-2-methylcyclohex-1-ol, alternatively, carvone (1-methyl-4-isopropenyl-6-cyclohex-1-en-2-one) can be hydrogenated, which is also commercially available. Suitable hydrogenation conditions correspond to those for the non-selective hydrogenation of carvonenone.

[0125] Compound:

[0126] One embodiment of the invention relates to a compound having the formula (Ia)

[0127]

[0128] or a stereoisomer thereof or a mixture of different stereoisomers,

[0129] wherein R is isopropylcarbonyl.

[0130] Another embodiment of the invention relates to a compound having the formula (Ib)

[0131]

[0132] or a stereoisomer thereof or a mixture of different stereoisomers,

[0133] wherein

[0134] R is a straight-chain or branched C1-C6 alkyl group.

[0135] Preferably, R is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl. More preferably, R is methyl or ethyl. Specifically, R is ethyl.

[0136] These compounds can be obtained by the methods described hereinafter in the context of the mixtures of the invention.

[0137] Mixture:

[0138] One embodiment of the present invention relates to a mixture comprising at least one compound having the formula (I)

[0139]

[0140] or a stereoisomer thereof or a mixture of different stereoisomers,

[0141] wherein

[0142] ---- represents a single bond or a double bond, and

[0143] R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group;

[0144] and

[0145] at least one compound having the formula (II)

[0146]

[0147] or a stereoisomer thereof or a mixture of different stereoisomers,

[0148] wherein

[0149] R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group.

[0150] Preferably, in compounds (I) and (II), R has the same meaning.

[0151] The above description of the preferred embodiments of compound (I) also applies to the case of the mixture with compound (II).

[0152] Thus, among compounds (Ia) and (Ib), compound (Ia) is preferred.

[0153] In a preferred embodiment, R is a straight-chain or branched C1-C6-alkyl group, wherein the C1-C6-alkyl group is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl. More preferably, R is methyl or ethyl.

[0154] In another preferred embodiment, R is a formyl group or a straight-chain or branched C1-C4-alkylcarbonyl group. More preferably, R is a straight-chain or branched C1-C4-alkylcarbonyl group, wherein the C1-C4-alkylcarbonyl group is preferably selected from methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl and tert-butylcarbonyl. Even more preferably, R is a C1-C3-alkylcarbonyl group, wherein the C1-C3-alkylcarbonyl group is preferably methylcarbonyl, ethylcarbonyl or isopropylcarbonyl. Particularly preferably, R is methylcarbonyl or ethylcarbonyl.

[0155] In a particularly preferred embodiment, the compound of formula (I) is a compound of formula (Ia), where R is a straight-chain or branched C1-C3-alkylcarbonyl, in particular methylcarbonyl, ethylcarbonyl or isopropylcarbonyl, and more particularly methylcarbonyl or ethylcarbonyl.

[0156] In a preferred embodiment, the mixture comprises a compound of formula (I) and a compound of formula (II) in a weight ratio in the range from 0.01:99.99 to 99.99:0.01.

[0157] In a more preferred embodiment, the mixture comprises a compound of formula (I) and a compound of formula (II) in a weight ratio in the range from 100:1 to 1:100, such as from 97:1 to 3:97 or from 94:5 to 5:94 or from 10:90 to 90:10, or from 11:89 to 89:11 or from 12:88 to 88:12, or from 13:87 to 87:13, or from 14:86 to 86:14, or from 15:85 to 85:15, or from 16:84 to 84:16, or from 17:83 to 83:17, or from 18:82 to 82:18, or from 19:81 to 81:19, or from 20:80 to 80:20.

[0158] Preferably, the amount of compound (I) exceeds the amount of compound (II). Thus, the weight ratio of the total amount of the compound of formula (I) to the total amount of the compound of formula (II) is particularly preferably in the range from 100:1 to 1:1, more particularly from 50:1 to 1:1, even more particularly from 35:1 to 2:1, and specifically from 25:1 to 3:1, such as from 20:1 to 4:1.

[0159] Compound (II) can be obtained by etherification or esterification of 2-hydroxy-1,4-cineole (which can be said to be compound (II) where R is hydrogen).

[0160] 2-Hydroxy-1,4-cineole can in turn be obtained from terpinene-4-ol (by epoxidation at the double bond). The acid-catalyzed rearrangement of the epoxide formed in this reaction gives 2-hydroxy-1,4-cineole. This synthetic route is described in WO2023 / 144219, WO 2018 / 210662, EP 0081892 or EP 0081893 and the documents cited therein. In the acid-catalyzed rearrangement of the epoxide, 5-hydroxy-5-isopropyl-2-methylcyclohexan-1-one is formed as a by-product, which can be dehydrated to give carvone (3-isopropyl-6-methylcyclohex-2-en-1-one; as described in the context of the process for obtaining compound (I), this is a compound that can be reduced to an alcohol from which compound (I) is prepared). Carvone may contain residual amounts of 2-hydroxy-1,4-cineole. If 2-hydroxy-1,4-cineole is not separated from carvone or from the alcohol obtained by its above-mentioned reduction (selectively at the carbonyl group or at both the carbonyl group and the C-C double bond), it remains in the esterification or etherification reactions of the alcohol obtained in the reduction of carvone, in which its OH group is acylated or alkylated together with the OH group of the alcohol. This gives a mixture of compounds (I) and (II); R is the same in these compounds.

[0161] If 2-hydroxy-1,4-cineole is provided in isolated form (rather than as a by-product in the above reaction), compound (II) can be obtained by etherification or esterification of 2-hydroxy-1,4-cineole. Suitable etherification or esterification conditions correspond to those described above for the synthesis of compound (I). Compound (II) can then be mixed with compound (I) in any desired ratio; R can also vary in compounds (I) and (II).

[0162] Thus, a mixture of at least one compound of formula I and at least one compound of formula II can be obtained directly from the reaction mixture or can be physically mixed in any desired ratio according to the end use in any suitable composition. However, for economic reasons, it is advantageous to provide a mixture of compounds (I) and (II) from the said reaction mixture.

[0163] Preferred embodiments of the invention relate to the use of the mixture for imparting to a composition the following fragrance notes: camphoraceous, citrusy, floral, herbal, ethereal, fresh, ionone-like, spicy, woody, carrot-like, junipery, peppery, warm, mentholated, cedarwood, minty, dandelion, earthy, food-like or any combination of two or more of these fragrance notes.

[0164] Another embodiment relates to a method for imparting an aromatic effect to a composition, which method comprises at least the step of adding the aforementioned mixture to the composition.

[0165] Another embodiment of the present invention relates to a mixture for imparting an aromatic effect to a composition, which mixture comprises at least one compound of formula (I) and at least one compound of formula (II).

[0166] In a further embodiment, the present invention relates to the use of the aforementioned mixture for enhancing the aroma of a composition.

[0167] In an embodiment of the present invention, the mixture is used as a perfume or as a component of a fragrance composition.

[0168] Suitable compositions are, for example, compositions for personal care, household care, industrial applications, and compositions for other applications, such as pharmaceutical compositions or crop protection compositions.

[0169] Preferably, the mixture according to the present invention is used in compositions selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

[0170] The compositions are described in more detail in the following paragraphs.

[0171] Compound (II):

[0172] Some compounds (II) are novel and are therefore also part of the present invention. Thus, the present invention relates to a compound of formula (II)

[0173]

[0174] or a stereoisomer thereof or a mixture of different stereoisomers,

[0175] wherein R is methyl, ethyl, ethylcarbonyl or isopropylcarbonyl.

[0176] Composition:

[0177] In an embodiment, the present invention relates to a composition which comprises a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II), and

[0178] (i) at least one aroma chemical (X) other than a compound of formula I, a compound of formula II or a stereoisomer thereof, or

[0179] (ii) at least one non-aromatic chemical carrier, or

[0180] (iii) both (i) and (ii).

[0181] Preferably, in this embodiment, the composition comprises a compound of formula (I) in a total amount in the range of ≥0.01 wt.% to ≤70.0 wt.% based on the total weight of the composition (if compound (II) is absent) or a mixture comprising a compound of formula (I) and a compound of formula (II).

[0182] Preferably, the composition is an aromatic composition, more preferably a fragrance composition.

[0183] Aromatic chemicals different from the compound of formula (I) and the compound of formula (II):

[0184] In one embodiment, the composition comprises at least one aromatic chemical different from the compound of formula (I) and the compound of formula (II).

[0185] Aromatic chemicals different from the compounds of formula (I) and (II) are also referred to as aromatic chemicals (X).

[0186] Due to their physical properties, the compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) can be well combined with aromatic chemicals different from the compound of formula (I) and the compound of formula (II) and other conventional components in an aromatic composition, especially a fragrance composition. This allows, for example, the production of an aromatic composition (preferably a fragrance composition) having novel and advantageous sensory properties. In particular, as already explained above, these compounds can provide a boosting effect for other aromatic chemicals such as fragrances.

[0187] Aromatic chemicals (X) are preferably selected from:

[0188] Geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indanyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indanyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styralyl acetate, octahydro-2,3,8,8-tetramethyl-2-naphthalenone 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-n-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E) and / or (Z)-3-methylcyclopentadecen-5-one, 15-pentadecen-11-olide and / or 15-pentadecen-12-olide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl) acetate, or 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.

[0189] In a preferred embodiment, the at least one aromatic chemical (X) is selected from methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, or methyl benzoate.

[0190] In another preferred embodiment, the at least one aromatic chemical (X) is selected from ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol), or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0191] Additional aromatic chemicals with which the compound of formula (I) can be combined to obtain the composition according to the invention can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Volumes I and II, Montclair, New Jersey, 1969, self-published or H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2016. Specifically, mention may be made of:

[0192] Extracts from natural raw materials such as essential oils, concretes, absolutes, resins, balsams, butters, tinctures, such as

[0193] Amber tincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise seed oil; Valerian oil; Basil oil; Evernia prunastri absolute; Bay oil; Artemisia argyi oil; Benzoin resin; Bergamot oil; Beeswax absolute; Birch tar; Bitter almond oil; Mentha piperita oil; Buchu leaf oil; Kahlua oil; Juniper oil; Acorus calamus oil; Camphor oil; Cananga oil; Cardamom oil; Chenopodium ambrosioides oil; Cinnamon oil; Cinnamon absolute; Castoreum absolute; Cedar leaf oil; Cedarwood oil; Cistus ladaniferus oil; Citronella oil; Lemon oil; Cubeb balsam; Cubeb balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Inula graveolens oil; Dill leaf oil; Dill seed oil; Eau de toilette absolute; Oakmoss absolute; Elemi oil; Tarragon oil; Citriodora oil; Eucalyptus oil; Anise oil; Pine needle oil; White pine oil; Colophony resin; Geranium oil; Grapefruit oil; Guaiac wood oil; Copaiba balsam; Copaiba balsam oil; Helichrysum italicum absolute; Helichrysum italicum oil; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Acorus calamus oil; Chamomilla recutita oil; Roman chamomile oil; Carrot seed oil; Chenopodium ambrosioides oil; Pine needle oil; Mentha spicata oil; Caraway oil; Labdanum oil; Labdanum absolute; Labdanum resin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Heracleum lanatum oil; Distilled lime oil; Pressed lime oil; Linalool oil; Litsea cubeba oil; Bay leaf oil; Nutmeg oil; Marjoram oil; Mandarin oil; Ocotea cymbarum oil; Mimosa absolute; Musk seed oil; Musk tincture; Clary sage oil; Nutmeg kernel oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Frankincense absolute; Frankincense oil; Bisabolol oil; Neroli absolute; Orange oil; Oregano oil; Palmarosa oil; Patchouli oil; Perilla oil; Peru balsam oil; Parsley leaf oil; Parsley seed oil; Orange leaf oil; Peppermint oil; Pepper oil; Piper nigrum oil; Pine oil; Mentha pulegium oil; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Salvia officinalis var. officinalis oil; Salvia officinalis var. latifolia oil; Sandalwood oil; Celery seed oil; Lavandula latifolia oil; Star anise oil; Styrax oil; Tagetes erecta oil; Fir oil; Tea tree oil; Turpentine oil; Thyme oil; Tolu balsam; Coumarin absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; Verbena oil; Vetiver oil; Juniper berry oil; Pomace oil; Absinthe oil; Wintergreen oil; Hyssop oil; Civet absolute; Cinnamon leaf oil; Cinnamon bark oil, and their fractions, or components isolated therefrom;

[0194] Individual perfumes from the group consisting of: hydrocarbons such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; aromadendrene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;

[0195] 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-methylenehept-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoct-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

[0196] 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; 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;

[0197] 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;

[0198] Aliphatic nitriles, such as 2-nonenitrile; 2-undecenenitrile; 2-tridecenenitrile; 3,12-tridecadienenitrile; 3,7-dimethyl-2,6-octadienenitrile; 3,7-dimethyl-6-octenenitrile;

[0199] Esters of aliphatic carboxylic acids such as formic acid (E) and (Z)-3-hexenyl ester; 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-methylvalerate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octynoate; methyl 2-nonynoate; allyl 2-isopentoxyacetate; methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

[0200] Acyclic terpenoid alcohols such as geraniol; nerol; linalool; lavandulol; geranylgeraniol; 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, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0201] Acyclic terpenoid 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; cyclic terpenoid alcohols such as menthol; isopulegol; α-terpineol; terpinene-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nobelol; cedrol; ambreinolide; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0202] Cyclic terpenic aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenthane-3-one; carvone; camphor; anisaldehyde; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-iso-methylionone; β-iso-methylionone; α-irone; α-damascone; β-damascone; β-damascenone; δ-damascone; γ-damascone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-germacratrien-3-one; α-sinensal; β-sinensal; acetylated cedarwood oil (methyl cedryl ketone);

[0203] Cyclic alcohols, such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isobornylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

[0204] 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)pent-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)pent-3-ol; 1-(2,2,6-trimethylcyclohexyl)hex-3-ol;

[0205] Cyclic and alicyclic ethers, such as cineole; methyl cedryl 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-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

[0206] Cyclic ketones 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-cyclopentadecene-1-one; 3-methyl-5-cyclopentadecanone; 3-methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-amylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indenone; 8-cyclohexadecen-1-one; 7-cyclohexadecen-1-one; (7 / 8)-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;

[0207] 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;

[0208] 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;

[0209] Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-amylcyclohexyl acetate; 4-tert-amylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl 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;

[0210] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

[0211] Esters of alicyclic carboxylic acids, such as allyl 3 - cyclohexylpropionate; allyl cyclohexyloxyacetate; methyl cis - and trans - dihydrojasmonate; methyl cis - and trans - jasmonate; methyl 2 - hexyl - 3 - oxocyclopentanecarboxylate; ethyl 2 - ethyl - 6,6 - dimethyl - 2 - cyclohexene - 1 - carboxylate; ethyl 2,3,6,6 - tetramethyl - 2 - cyclohexene - 1 - carboxylate; ethyl 2 - methyl - 1,3 - dioxolane - 2 - acetate;

[0212] Aryl - aliphatic alcohols, such as benzyl alcohol; 1 - phenylethanol, 2 - phenylethanol, 3 - phenyl - 1 - propanol; 2 - phenyl - 1 - propanol; 2 - phenoxyethanol; 2,2 - dimethyl - 3 - phenyl - 1 - propanol; 2,2 - dimethyl - 3 - (3 - methylphenyl) - 1 - propanol; 1,1 - dimethyl - 2 - phenylethanol; 1,1 - dimethyl - 3 - phenyl - 1 - propanol; 1 - ethyl - 1 - methyl - 3 - phenyl - 1 - propanol; 2 - methyl - 5 - phenyl - 1 - pentanol; 3 - methyl - 5 - phenyl - 1 - pentanol; 3 - phenyl - 2 - propen - 1 - ol; 4 - methoxy - benzyl alcohol; 1 - (4 - isopropylphenyl)ethanol;

[0213] Esters of aryl - 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;

[0214] Aryl - aliphatic ethers, such as 2 - phenylethyl methyl ether; 2 - phenylethyl isopentyl ether; 2 - phenylethyl 1 - ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydroatropaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6 - trimethyl - 4 - phenyl - 1,3 - dioxane; 4,4a,5,9b - tetrahydro - indeno[1,2 - d] - m - dioxin; 4,4a,5,9b - tetrahydro - 2,4 - dimethyl - indeno[1,2 - d] - m - dioxin;

[0215] Aromatic and araliphatic aldehydes, such as benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydroatropic aldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert-butylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal; cinnamaldehyde; α-butylcinnamaldehyde; α-amylcinnamaldehyde; α-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal;

[0216] 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-naphthyl)ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2'-naphthaleneethanone;

[0217] Aromatic and aliphatic carboxylic acids and their esters, such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate;

[0218] Nitrogen-containing aromatic compounds, such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamitrile; 3-methyl-5-phenyl-2-pentenenitrile; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; methyl-N-methylanthranilate; Schiff base of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy-3-isopropyl-pyrazine; 2-isobutyl-3-methoxypyrazine;

[0219] Phenols, phenyl ethers and phenyl esters, such as estragole; anethole; eugenol; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether; β-naphthyl methyl ether; β-naphthyl ethyl ether; β-naphthyl isobutyl ether; 1,4-dimethoxybenzene; eugenol acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresyl phenylacetate;

[0220] 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;

[0221] 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.

[0222] The aromatic chemicals (X) used in the composition are obtained from known commercial sources and purchased from Germany.

[0223] In a preferred embodiment, the composition comprises a compound having the formula (I) or a mixture comprising a compound having the formula (I) and a compound having the formula (II) and at least one aroma chemical (X), wherein the at least one aroma chemical (X) different from the compounds having the formulas (I) and (II) is preferably selected from the group consisting of geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis-isomer content of more than 60 wt.%), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, linalool, 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-indanyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indanyl acetate, citronellol, citronellyl acetate, citronellol, geraniol, tetrahydrogeraniol, vanillin, linalyl acetate, styralyl acetate, octahydro-2,3,8,8-tetramethyl-2-naphthalenone, 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-n-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadeca-5-enone, (Z)-3-methylcyclopentadeca-5-enone, 15-pentadecen-11-olide, 15-pentadecen-12-olide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, citral, citronellal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably having 70 wt.%, or more cis-isomer content), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl) acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-n-methylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0224] Non-aromatic chemical carriers:

[0225] The non-aromatic chemical carriers in the compositions of the present invention are preferably selected from the group consisting of surfactants, oil components, antioxidants, deodorant active agents, and solvents.

[0226] Preferably, the at least one non-aromatic chemical carrier is a compound, a mixture of compounds, or other additives that do not have sensory properties or do not have significant sensory properties. The non-aromatic chemical carrier can be used to dilute and / or immobilize the compound having formula (I) as defined above or a mixture comprising the compound having formula (I) and the compound having formula (II) and - optionally the at least one aromatic chemical (X) (if included in the composition).

[0227] The non-aromatic chemical carriers in the compositions of the present invention are preferably selected from surfactants, oil components, solvents, or any mixture of two or more of the foregoing.

[0228] Solvents:

[0229] In the context of the present invention, "solvent" is used to dilute the compound having formula (I) used according to the present invention or a mixture comprising the compound having formula (I) and the compound having formula (II) without having its own aroma.

[0230] The amount of one or more solvents is adjusted according to the composition and represents a routine task for those skilled in the art.

[0231] Preferably, the solvent is present in the composition in a total amount of from 0.01 wt.% to 99.0 wt.%, more preferably from 0.05 wt.% to 95.0 wt.%, still more preferably from 0.1 wt.% to 80.0 wt.%, most preferably from 0.1 wt.% to 70.0 wt.%, especially from 0.1 wt.% to 60.0 wt.%, based on the total weight of the composition.

[0232] In a preferred embodiment, the composition comprises from 0.05 wt.% to 10 wt.%, more preferably from 0.1 wt.% to 5 wt.%, still more preferably from 0.2 wt.% to 3 wt.% of total solvent, based on the total weight of the composition. In yet another preferred embodiment of the present invention, the composition comprises from 20 wt.% to 70 wt.%, more preferably from 25 wt.% to 50 wt.% of total solvent, based on the total weight of the composition.

[0233] Preferred solvents are selected from ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2 - butanediol, dipropylene glycol, triethyl citrate, isopropyl myristate, or any mixture of two or more of the foregoing.

[0234] In a preferred embodiment, the composition comprises a compound having formula (I) or a mixture comprising a compound having formula (I) and a compound having formula (II), and at least one solvent and optionally at least one aromatic chemical (X).

[0235] Oil component:

[0236] Preferably, the total oil component is present in an amount of from 0.1 to 80 wt.%, more preferably from 0.5 to 70 wt.%, still more preferably from 1 to 60 wt.%, even more preferably from 1 to 50 wt.%, particularly from 1 to 40 wt.%, more particularly from 5 to 25 wt.% and specifically from 5 to 15 wt.%, based on the total weight of the composition.

[0237] Preferably, the oil component is selected from Guerbet alcohols based on fatty alcohols containing 6 to 18, preferably 8 to 10 carbon atoms, and other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, and erucyl erucate. Also suitable are esters of C18-C38 alkyl-hydroxycarboxylic acids with straight-chain or branched C6-C22 fatty alcohols, more particularly dioctyl malate, esters of straight-chain and / or branched fatty acids with polyols (such as propylene glycol, dimer diol or trimer triol), triglycerides based on C6-C10 fatty acids, liquid mixtures of glycerol monoesters, glycerol diesters and glycerol triesters based on C6-C18 fatty acids, esters of C6-C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, straight-chain and branched C6-C22 fatty alcohol carbonates, such as dicaprylyl carbonate ( CC), Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10 carbon atoms, esters of benzoic acid with straight-chain and / or branched C6 to C22 alcohols (such as TN), straight-chain or branched, symmetrical or asymmetrical dialkyl ethers in which each alkyl contains 6 to 22 carbon atoms, such as dioctyl ether ( OE), ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof.

[0238] In a preferred embodiment, the composition comprises a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) and at least one oil component and optionally at least one fragrance chemical (X).

[0239] Antioxidants:

[0240] It should be understood that antioxidants can inhibit or prevent undesirable changes in the composition to be protected caused by oxygen effects and other oxidation processes. In most cases, the role of antioxidants is that they act as free radical scavengers for free radicals generated during autoxidation.

[0241] In a preferred embodiment, the antioxidant is selected from

[0242] · Amino acids (such as glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives,

[0243] · Imidazoles (such as urocanic acid) and their derivatives,

[0244] · Peptides, such as D,L-carnosine, D-carnosine, L-carnosine (= β-alanyl-L-histidine) and their derivatives,

[0245] · Carotenoids, carotenes (such as α-carotene, β-carotene, lycopene, lutein) or their derivatives,

[0246] · Chlorogenic acid and its derivatives,

[0247] · Alpha-lipoic acid and its derivatives (such as dihydrolipoic acid),

[0248] · Aurothioglucose, propylthiouracil and other thiols (such as thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, pentyl, butyl and lauryl, palmitoyl, oleyl, γ-linolenyl, cholesteryl and glyceryl esters) and their salts,

[0249] · Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

[0250] · Sulfoximine compounds (such as buthionine sulfoximine, homocysteine sulfoximine, buthionine sulfone, penta-, hexa-, heptathionine sulfoximine),

[0251] · (Metal) chelating agents (such as α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

[0252] · Alpha-hydroxy acids (such as citric acid, lactic acid, malic acid),

[0253] · Humic acids, bile acids, bile extracts, bilirubin, biliverdin, boldine (= alkaloid from the plant Boldo tree), Boldo extract,

[0254] · EDTA, EGTA and their derivatives,

[0255] · Unsaturated fatty acids and their derivatives (such as gamma-linolenic acid, linoleic acid, oleic acid),

[0256] · Folic acid and its derivatives,

[0257] · Ubiquinone and ubiquinol and their derivatives,

[0258] · Vitamin C and derivatives (such as ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

[0259] · Tocopherol and derivatives (such as vitamin E acetate),

[0260] · Vitamin A and derivatives (such as vitamin A palmitate),

[0261] · Coniferyl benzoate of benzoin, rutinic acid and its derivatives, alpha-glycosylrutin, ferulic acid, furoylglucitol,

[0262] · Butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA),

[0263] · Nordihydroguaiaretic acid, nordihydroguaiaretic acid, trihydroxybenzophenone, uric acid and its derivatives, mannose and its derivatives,

[0264] · Superoxide dismutase,

[0265] · Zinc and its derivatives (such as ZnO, ZnSO4),

[0266] · Selenium and its derivatives (such as selenomethionine),

[0267] · Stilbene and its derivatives (such as, oxidized stilbene, trans-oxidized stilbene),

[0268] or a mixture of two or more of the foregoing.

[0269] In a preferred embodiment, the antioxidant is selected from pentaerythritol, tetra-di-tert-butylhydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ascorbyl palmitate, tocopherol, or a mixture of two or more of the foregoing.

[0270] Preferably, the composition according to the invention comprises a total amount of antioxidant of from 0.001 to 25 wt.-%, preferably from 0.005 to 10 wt.-%, more preferably from 0.01 to 8 wt.-%, even more preferably from 0.025 to 7 wt.-%, and even more preferably from 0.05 to 5 wt.-% based on the total weight of the composition.

[0271] In a preferred embodiment, the composition comprises a compound having formula (I) or a mixture comprising a compound having formula (I) and a compound having formula (II), at least one antioxidant, and optionally at least one fragrance chemical (X).

[0272] Deodorant active agent

[0273] Deodorant compositions (deodorants and antiperspirants) counteract, mask or eliminate body odor. Body odor is formed by the action of skin bacteria on apocrine sweat, which results in the formation of degradation products with unpleasant odors.

[0274] Preferably, the deodorant active agent is selected from antiperspirants, esterase inhibitors, antibacterial agents, or a mixture of two or more of the foregoing.

[0275] Suitable antiperspirants are selected from salts of aluminum, zirconium or zinc. Examples are aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complex compounds (e.g., with 1,2 - propanediol), aluminum hydroxy allantoin, aluminum chloride tartrate, zirconium trichlorohydrex gly, zirconium tetrachlorohydrex gly, zirconium pentachlorohydrex gly and their complex compounds (e.g., with amino acids such as glycine). Aluminum chlorohydrate, zirconium tetrachlorohydrex gly, zirconium pentachlorohydrex gly, or their complex compounds are preferably used.

[0276] Preferably, the antiperspirant is selected from aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxy allantoin, aluminum chloride tartrate, zirconium trichlorohydrex gly, zirconium tetrachlorohydrex gly, zirconium pentachlorohydrex gly, or a mixture of two or more of the foregoing.

[0277] When sweat is present in the axillary region, extracellular enzymes - esterases, mainly proteases and / or lipases, are formed by bacteria and decompose the esters present in the sweat, releasing odors in the process. Suitable esterase inhibitors are, for example, trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate. Esterase inhibitors inhibit enzyme activity and thus reduce odor formation. Free acids may be released by the cleavage of the citrate esters and lower the pH of the skin to an extent where the enzyme is inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfates or phosphates, dicarboxylic acids and their esters, such as glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters, such as citric acid, malic acid, tartaric acid or diethyl tartrate, zinc glycinate and a mixture of two or more of the foregoing.

[0278] Preferably, the esterase inhibitor is selected from trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartrate, zinc glycinate, or a mixture of two or more of the foregoing.

[0279] Preferably, the composition according to the invention comprises a total amount of esterase inhibitor in the range of from 0.01 to 20 wt.-%, preferably from 0.1 to 10 wt.-% and more particularly from 0.5 to 5 wt.-%, based on the total weight of the composition.

[0280] As used herein, the term "antimicrobial agent" encompasses substances having bactericidal and / or bacteriostatic properties. Typically, these substances act on Gram-positive bacteria, such as 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'-methylenebis(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides such as salicylic acid-n-octylamide or salicylic acid-n-decylamide.

[0281] Preferably, the antimicrobial agent is selected from 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'-methylenebis(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides, or a mixture of two or more of the foregoing.

[0282] Preferably, the composition according to the invention comprises a total amount of one or more antimicrobial agents in the range of from 0.01 to 5 wt.%, preferably from 0.1 to 2 wt.%, based on the total weight of the composition.

[0283] In a preferred embodiment, the composition comprises a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) and at least one deodorizing active agent and optionally at least one aromatic chemical (X).

[0284] Surfactant

[0285] Preferably, the surfactant is selected from anionic, nonionic, cationic, amphoteric, zwitterionic surfactants, or a mixture of two or more of the foregoing. More preferably, the surfactant is an anionic surfactant.

[0286] Preferably, the composition according to the invention contains one or more surfactants in a total amount of from 0 to 40 wt.%, more preferably from 0 to 20 wt.%, more preferably from 0.1 to 15 wt.%, and especially from 0.1 to 10 wt.%, based on the total weight of the composition.

[0287] Preferred nonionic surfactants are fatty alcohol polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, fatty acid polyethylene glycol esters, fatty acid amide polyethylene glycol ethers, fatty amine polyethylene glycol ethers, alkoxylated triglycerides, mixed ethers and mixed formaldehyde acetals, optionally partially oxidized alkyl(ene) oligosaccharides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolysates (especially wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyethylene glycol ether chains, they may have a conventional homolog distribution, but they preferably have a narrow range of homolog distribution.

[0288] Zwitterionic surfactants are surface-active compounds which contain in the molecule at least one quaternary ammonium group and at least one COO(−) or SO3(−) group.

[0289] Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethylglycine ammonium, for example cocoalkyldimethylglycine ammonium, N-acylaminopropyl-N,N-dimethylglycine ammonium, for example cocoacylaminopropyldimethylglycine ammonium, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoline, which contain 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethylhydroxyethylcarboxymethyl glycinate. Fatty acid amide derivatives known by the CTFA name of cocoamidopropyl betaine are particularly preferred.

[0290] Amphoteric surfactants are also suitable, especially as co-surfactants. Amphoteric surfactants are surface-active compounds which, in addition to a C8 to C18 alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO3H group and are capable of forming an inner salt. Examples of suitable amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, which contain about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-coconut alkylaminopropionates, coconut acylaminoethylaminopropionates and acylsarcosines.

[0291] Anionic surfactants are characterized by water-soluble anionic groups (such as, for example, 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 especially alkyl sulfates, alkyl ether sulfates, alkyl ether carboxylates, acyl hydroxyethyl sulfonates, acyl sarcosinates, in the form of their alkali metal, ammonium or alkanolammonium salts, acyl taurines containing straight-chain C 12 -C 18 alkyl or acyl groups, and sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.

[0292] Particularly suitable cationic surfactants are quaternary compounds, preferably ammonium halides, more especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. In addition, readily biodegradable quaternary ester compounds, such as, for example, dialkylammonium methyl sulfates and methyl hydroxyalkyl dialkoxyalkylammonium methyl sulfates sold under the name Stepantexe and the corresponding series of products, can be used as cationic surfactants. "Ester quats" are generally understood to be quaternized fatty acid triethanolamine ester salts. They 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 invention are quaternized protein hydrolysates.

[0293] Due to the characteristic sensory properties of the compounds of formula (I), as well as their tenacity, persistence and stability, it can in particular be used to provide an odor, preferably a fragrance effect, to surfactant-containing compositions such as detergents (especially laundry care products and multi-purpose cleaners). It can preferably be used to impart to the surfactant-containing composition a long-lasting fragrance note selected from the group consisting of: fresh fragrance note, mint fragrance note, stale fragrance note, carrot-like fragrance note, natural fragrance note, root fragrance note, violet fragrance note, powdery fragrance note, floral fragrance note, woody fragrance note, warm fragrance note, ionone fragrance note, fruity fragrance note, camphor fragrance note, citrus fragrance note, herbal fragrance note, etheric fragrance note, gourmand fragrance note, anise fragrance note, ambergris-like fragrance note, animalic fragrance note, civet fragrance note, soft fragrance note, incense fragrance note, musty fragrance note, fatty fragrance note, tobacco fragrance note, green leaf fragrance note.

[0294] In a preferred embodiment, the composition comprises a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) and at least one surfactant and optionally at least one aroma chemical (X).

[0295] Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions and products for oral and dental hygiene), hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

[0296] Perfume compositions can be selected from fine fragrances, air fresheners in liquid form, gel form or applied to a solid carrier, aerosol sprays, scented cleaners, perfume candles, or oils such as lamp oil or oil for massage.

[0297] Examples of fine fragrances are perfume extracts, eau de parfum, eau de toilette, cologne, solid perfume and eau de parfum concentrée.

[0298] The body care compositions include cosmetic compositions and products for oral and dental hygiene, and may be selected from aftershaves, pre-shave products, splash colognes, 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 makeup milks, such as skin creams and emulsions, face creams and emulsions, sunscreens and emulsions, after-sun creams and emulsions, hand creams and emulsions, foot creams and emulsions, depilatory creams and emulsions, aftershave creams and emulsions, self-tanning creams and emulsions, hair care products, such as hairsprays, hair gels, hair styling emulsions, hair conditioners, shampoos, permanent and semi-permanent hair colorants, hair styling compositions, such as cold waves and hair smoothing compositions, hair growth oils, hair pomades and hair creams, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks and deodorant creams; decorative cosmetic products, such as eyeliner, eyeshadow, nail polish, foundation, lipsticks and mascaras; and products for oral and dental hygiene, such as toothpaste, dental floss, mouthwash, breath fresheners, dental foams, dental gels and dental strips.

[0299] The hygiene products may be selected from incense sticks, insecticides, repellents, propellants, rust removers, fragrant cleansing wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, handkerchief tissues, dishwashing agents and deodorants.

[0300] The cleaning compositions, such as those for solid surfaces, may be selected from aromatic acidic, alkaline and neutral cleaners, such as floor cleaners, window cleaners, dishwashing compositions for both hand and machine washing, bath and hygiene cleaners, scrubbing milks, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes, such as furniture polishes, floor waxes, shoe polishes, disinfectants, surface disinfectants and hygiene cleaners, brake cleaners, pipe cleaners, scale removers, grill and oven cleaners, algae and moss removers, mold removers, facade cleaners.

[0301] The textile detergent compositions may be selected from liquid detergents, powder detergents, laundry pre-treatments (such as bleaches, soaks and stain removers), fabric softeners, washing soaps, washing tablets.

[0302] Food means raw, cooked or processed edible substances, ice, beverages or ingredients intended or suitable for human consumption, in whole or in part, or chewing gums, gummies, jellies, and candies.

[0303] A food supplement is a product intended for ingestion and containing dietary ingredients intended to add additional nutritional value to the diet. Dietary ingredients can be one or any combination of the following substances: vitamins, minerals, herbs or other botanical preparations, amino acids, food substances for people to supplement the diet by increasing total dietary intake, concentrates, metabolites, components, or extracts. Food supplements can be seen in various forms such as tablets, capsules, soft gels, soft capsules, liquids, or powders.

[0304] A pharmaceutical composition includes a composition intended for the diagnosis, cure, mitigation, treatment, or prevention of a disease, and an article (other than food) intended to affect the structure or any function of the body of a human or other animal.

[0305] A crop protection composition includes a composition intended for managing plant diseases, weeds, and other pests (both vertebrates and invertebrates) that damage agricultural crops and forestry.

[0306] Preferably, the composition according to the present invention further comprises at least one adjuvant selected from the group consisting of: preservatives, abrasives, anti-acne agents, anti-skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, irritation relievers, astringents, antiperspirants, fungicides, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, care agents, depilatory agents, emulsifiers, enzymes, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizers, anti-foaming substances, foam promoters, fungicides, gelling agents, gel-forming agents, hair care agents, hair styling agents, hair smoothing agents, humectants, moisturizing substances, wetting substances, bleaching agents, strengthening agents, detergents, optical brighteners, impregnating agents, anti-stain agents, anti-friction agents, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, covering agents, polishing agents, luminescent agents, polymers, powders, proteins, fatliquors, stripping agents, silicones, skin soothers, skin cleansing agents, skin care agents, skin healing agents, skin brighteners, skin protectants, skin softeners, coolants, skin coolants, warmants, skin warmants, stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color fixatives, pigments, corrosion inhibitors, polyols, electrolytes, and silicone derivatives.

[0307] A method for preparing a composition and imparting an aromatic effect to the composition:

[0308] One embodiment of the present invention relates to a method for preparing a composition that contains a compound having formula (I) or a mixture containing a compound having formula (I) and a compound having formula (II), and

[0309] (i) At least one aroma chemical (X) other than the compounds according to the invention, in particular compounds of formula I, compounds of formula II, including their stereoisomers, or

[0310] (ii) At least one non-aromatic chemical carrier, or

[0311] Both (i) and (ii).

[0312] For example, the method can be carried out by mixing a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) with:

[0313] (i) At least one aromatic compound (X) other than the compounds according to the invention, in particular compounds of formula I, compounds of formula II, including their stereoisomers, or

[0314] (ii) At least one non-aromatic chemical carrier, or

[0315] (iii) Both (i) and (ii).

[0316] The present invention also relates to a method for enhancing the aromatic effect of a composition, wherein the method comprises incorporating a compound of formula (I) or a mixture comprising a compound of formula (I) and a compound of formula (II) into the composition.

[0317] 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 an aroma dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition, the method comprising including a compound of formula (I) in the perfume composition, the body care composition, the hygiene product, the cleaning composition, the textile detergent composition, the composition for an aroma dispenser, the food, the food supplement, the pharmaceutical composition or the crop protection composition.

[0318] 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 an aroma dispenser, a food, a food supplement, a pharmaceutical composition or a crop protection composition a fragrance reminiscent of a fresh fragrance note, a mint fragrance note, a stale fragrance note, a carrot-like fragrance note, a natural fragrance note, a root fragrance note, a violet fragrance note, a powdery fragrance note, a floral fragrance note, a woody fragrance note, a warm fragrance note, an ionone fragrance note, a fruity fragrance note, a camphor fragrance note, a citrus fragrance note, a herbal fragrance note, an etheric fragrance note, a gourmand fragrance note, an anise fragrance note, an ambrettolide-like fragrance note, an animalic fragrance note, a civet fragrance note, a soft fragrance note, an incense fragrance note, a musty fragrance note, a fatty fragrance note, a tobacco fragrance note, a green leafy fragrance note, a spicy fragrance note, an acidic fruity fragrance note, a juniper fragrance note, a pepper fragrance note, a spearmint fragrance note, a cedarwood fragrance note, a dandelion fragrance note, an earthy fragrance note, a food-like fragrance note, or a combination of two or more fragrance notes, the method comprising including in the perfume composition, the body care composition, the hygiene product, the cleaning composition, the textile detergent composition, the composition for an aroma dispenser, the food, the food supplement, the pharmaceutical composition, or the crop protection composition a compound having formula (I).

[0319] amount

[0320] Typically, the total amount of the compound having formula (I) and the compound having formula (II) in the compositions, methods and uses according to the present invention is typically adapted to the particular intended use or intended application and can thus vary within a wide range. Generally, conventional standard commercial amounts for aroma chemicals, preferably for fragrances, are used.

[0321] Preferably, the composition according to the present invention comprises, based on the total weight of the composition, from 0.001 to 99.9 wt.% of the total amount of the compound having formula (I).

[0322] In particular, the composition comprises, based on the total weight of the composition, from 0.001 to 99.5 wt.%, preferably from 50 to 99 wt.%, more preferably from 80 to 95 wt.% and in particular from 90 to 95 wt.% of the total amount of the compound having formula (I) or a mixture with the compound having formula (II).

[0323] In particular, the composition comprises, based on the total weight of the composition, from 0.005 to 80 wt.%, preferably from 0.1 to 30 wt.%, more preferably from 1 to 20 wt.% and in particular from 5 to 15 wt.% of the total amount of the compound having formula (I) or a mixture thereof with the compound having formula (II).

[0324] In particular, the composition comprises, based on the total weight of the composition, from 0.001 to 20 wt.%, preferably from 0.005 to 6 wt.%, more preferably from 0.05 to 4 wt.% and in particular from 0.1 to 3 wt.% in total of a compound of formula (I) or a mixture thereof with a compound of formula (II).

[0325] Examples

[0326] In the following, a list of examples is provided to further illustrate the disclosure and is not intended to limit the disclosure to the specific examples listed below

[0327] 1. At least one compound of formula (I)

[0328]

[0329] or a stereoisomer thereof or a mixture of different stereoisomers thereof,

[0330] wherein,

[0331] ---- represents a single bond or a double bond,

[0332] R is a straight-chain or branched C1-C6-alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl

[0333] Use as a fragrance chemical; or use for imparting a fragrance effect to a composition.

[0334] 2. The use according to Example 1, wherein the compound of formula (I) is a compound of formula (Ia) (i.e., the compound (I) wherein ---- is a single bond),

[0335]

[0336] or a stereoisomer thereof or a mixture of different stereoisomers thereof,

[0337] wherein,

[0338] R is a straight-chain or branched C1-C6-alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl.

[0339] 3. The use according to Example 1, wherein the compound of formula (I) is a compound of formula (Ib) (i.e., the compound (I) wherein ---- is a double bond)

[0340]

[0341] or a stereoisomer thereof or a mixture of different stereoisomers thereof,

[0342] wherein

[0343] R is a straight-chain or branched C1-C6 alkyl group, a formyl group, or a straight-chain or branched C1-C4 alkylcarbonyl group.

[0344] 4. The use according to any one of embodiments 1 to 3, wherein R is a straight-chain or branched C1-C6 alkyl group, and is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

[0345] 5. The use according to embodiment 4, wherein R is methyl or ethyl.

[0346] 6. The use according to any one of embodiments 1 to 3, wherein R is a formyl group, or a straight-chain or branched C1-C4 alkylcarbonyl group.

[0347] 7. The use according to embodiment 6, wherein R is a straight-chain or branched C1-C4 alkylcarbonyl group, and is preferably selected from methylcarbonyl or ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl or tert-butylcarbonyl.

[0348] 8. The use according to embodiment 7, wherein R is a straight-chain or branched C1-C3 alkylcarbonyl group, particularly methylcarbonyl, ethylcarbonyl or isopropylcarbonyl, and specifically methylcarbonyl or ethylcarbonyl.

[0349] 9. The use according to any one of embodiments 1, 2 and 6 to 8, wherein the compound of formula (I) is a compound of formula (Ia), wherein R is a straight-chain or branched C1-C3 alkylcarbonyl group, preferably methylcarbonyl, ethylcarbonyl or isopropylcarbonyl, and more preferably methylcarbonyl or ethylcarbonyl.

[0350] 10. The use according to any one of the foregoing embodiments, wherein the compound of formula (I) is used in admixture with: a compound of formula (II)

[0351]

[0352] or a stereoisomer thereof or a mixture of different stereoisomers,

[0353] wherein

[0354] R is as defined in any one of embodiments 1 and 4 to 9; wherein preferably, R has the same meaning in the compounds of formula (I) and (II).

[0355] 11. The use according to any one of the foregoing embodiments, which is as a fragrance or for imparting a fragrance to a composition.

[0356] 12. A method for imparting an aromatic effect to a composition, the method comprising at least the following steps: adding at least one compound of formula (I) according to any one of Examples 1 to 9 or a mixture according to Example 10 to the composition to be aromatized, or mixing at least one compound of formula (I) according to any one of Examples 1 to 9 or a mixture according to Example 10 simultaneously or continuously with other components of the composition, or mixing at least one compound of formula (I) according to any one of Examples 1 to 9 or a mixture according to Example 10 with a preformed mixture of a part of the other components of the composition.

[0357] 13. Use or method according to any one of Examples 1 to 12, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

[0358] 14. Use or method according to any one of Examples 1 to 13, wherein the aromatic effect is selected from fresh notes, minty notes, stale notes, carrot-like notes, natural notes, rooty notes, violet notes, powdery notes, floral notes, woody notes, warm notes, ionone notes, fruity notes, camphor notes, citrus notes, herbal notes, etheric notes, gourmand notes, anise notes, ambrettolide-like notes, animal notes, civet notes, soft notes, incense notes, musty notes, fatty notes, tobacco notes, green leafy notes, spicy notes, acid fruity notes, juniper notes, pepper notes, spearmint notes, cedarwood notes, dandelion notes, earthy notes, food-like notes, or a combination of two or more notes.

[0359] 15. Use or method according to any one of Examples 1 to 14, wherein the compounds of formula (I) are present in a total amount in the range of ≥ 0.01 wt.-% to ≤ 70.0 wt.-% based on the total weight of the composition.

[0360] 16. A compound of formula (Ia)

[0361]

[0362] or a stereoisomer thereof or a mixture of different stereoisomers,

[0363] wherein R is isopropylcarbonyl.

[0364] 17. A compound of formula (Ib)

[0365]

[0366]

[0367] or a stereoisomer thereof,

[0368] wherein,

[0369] R is a straight-chain or branched C1-C6-alkyl group, wherein R is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

[0370] 18. A compound of formula (Ib), wherein R is methyl or ethyl, and preferably ethyl.

[0371] 19. A composition comprising at least one compound of formula (I) according to any one of Examples 1 to 9, and (i) at least one fragrance chemical (X) different from the compound of formula (I), or

[0372] (ii) at least one non-fragrance chemical carrier, or

[0373] (iii) both (i) and (ii).

[0374] 20. The composition according to Example 19, wherein the at least one compound of formula (I) is present in an amount in the range of ≥0.01 wt.-% to ≤70.0 wt.-% based on the total weight of the composition.

[0375] 21. The composition according to any one of Examples 19 or 20, wherein the at least one non-fragrance chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant active agents, or solvents.

[0376] 22. The composition according to any one of Examples 19 to 21, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

[0377] 23. The composition according to any one of embodiments 19 to 22, which comprises at least one compound of formula (I) according to any one of claims 1 to 9, at least one fragrance chemical (X) different from the compound of formula (I), and optionally at least one non-fragrance chemical carrier, wherein the at least one fragrance chemical (X) different from the compound of formula (I) is selected from the group consisting of: geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis-isomer content of more than 60 wt.%), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, linalool, 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-indanyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indanyl acetate, citronellol, citronellyl acetate, citronellol, geraniol, tetrahydrogeraniol, vanillin, linalyl acetate, styralyl acetate, octahydro-2,3,8,8-tetramethyl-2-naphthalenone, 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-n-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadeca-5-enone, (Z)-3-methylcyclopentadeca-5-enone, 15-pentadecen-11-olide, 15-pentadecen-12-olide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, citral, citronellal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably having 70 wt.%, or more cis-isomer content), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl) acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-nor-methylionone, β-iso-methylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0378] 24. The composition according to any one of embodiments 18 to 22, wherein these non-aromatic chemical carriers are selected from the group consisting of surfactants, emollients, and solvents, and wherein these solvents are selected from the group consisting of: ethanol, isopropanol, propylene glycol, dipropylene glycol, 1,2-butanediol, diethylene glycol monoethyl ether, glycerol, diethyl phthalate, isopropyl myristate, triethyl citrate, and benzyl benzoate.

[0379] 25. A mixture comprising at least one compound of formula (I)

[0380]

[0381] or a stereoisomer thereof or a mixture of different stereoisomers,

[0382] wherein

[0383] ---- represents a single bond or a double bond, and

[0384] R is a straight-chain or branched C1-C6-alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl;

[0385] and

[0386] at least one compound of formula (II)

[0387]

[0388] or a stereoisomer thereof or a mixture of different stereoisomers,

[0389] wherein

[0390] R is a straight-chain or branched C1-C6 alkyl, formyl, or straight-chain or branched C1-C4-alkylcarbonyl;

[0391] wherein in the compounds of formula (I) and (II), R preferably has the same meaning.

[0392] 26. The mixture according to embodiment 25, wherein R is a linear or branched C1-C6-alkyl group; wherein R is preferably selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

[0393] 27. The mixture according to embodiment 26, wherein R is methyl or ethyl.

[0394] 28. The mixture according to embodiment 25, wherein R is formyl, or a linear or branched C1-C4-alkylcarbonyl group.

[0395] 29. The mixture according to embodiment 28, wherein R is a linear or branched C1-C4-alkylcarbonyl group; wherein R is preferably selected from methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, or tert-butylcarbonyl.

[0396] 30. The mixture according to embodiment 29, wherein R is a linear or branched C1-C 3- alkylcarbonyl group; wherein R is preferably methylcarbonyl, ethylcarbonyl or isopropylcarbonyl, and more preferably methylcarbonyl or ethylcarbonyl.

[0397] 31. The mixture according to any one of embodiments 25 to 30, wherein the weight ratio of the total amount of the compound having formula (I) to the total amount of the compound having formula (II) is in the range of 99.99:0.01 to 0.01:99.99, preferably 100:1 to 1:1, more preferably 50:1 to 1:1, especially 35:1 to 2:1, and more especially 25:1 to 3:1, for example 20:1 to 4:1.

[0398] 32. A composition comprising,

[0399] (i) the mixture according to any one of embodiments 25 to 31, and

[0400] (ii) at least one aromatic chemical (X) other than the compounds having formula (I) and (II), or

[0401] (iii) at least one non-aromatic chemical carrier, or

[0402] (iv) both (ii) and (iii).

[0403] 33. The composition according to embodiment 32, wherein the compounds (I) and (II) are present in a total amount in the range of ≥0.01 wt.-% to ≤70.0 wt.-% based on the total weight of the composition.

[0404] 34. The composition according to any one of embodiments 32 or 33, wherein at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant active agents, or solvents.

[0405] 35. The composition according to any one of embodiments 32 to 34, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

[0406] 36. The composition according to any one of embodiments 32 to 35, which comprises a mixture according to any one of embodiments 24 to 30, at least one aroma chemical (X) different from the compounds of formula (I) and (II), and optionally at least one non-aromatic chemical carrier, wherein the at least one aroma chemical (X) different from the compounds of formula (I) and (II) is selected from the group consisting of geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis-isomer content of more than 60 wt.%), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, linalool, 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-indanyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indanyl acetate, citronellol, citronellyl acetate, citronellol, geraniol, tetrahydrogeraniol, vanillin, linalyl acetate, styralyl acetate, octahydro-2,3,8,8-tetramethyl-2-naphthalenone, 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-n-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadec-5-enone, (Z)-3-methylcyclopentadec-5-enone, 15-pentadecen-11-olide, 15-pentadecen-12-olide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, citral, citronellal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably having 70 wt.%, or more cis-isomer content), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl) acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-nor-methylionone, β-iso-methylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0407] 37. The composition according to any one of embodiments 32 to 36, wherein these non-aromatic chemical carriers are selected from the group consisting of surfactants, emollients, and solvents, and wherein these solvents are selected from the group consisting of: ethanol, isopropanol, propylene glycol, dipropylene glycol, 1,2-butanediol, diethylene glycol monoethyl ether, glycerol, diethyl phthalate, isopropyl myristate, triethyl citrate, and benzyl benzoate.

[0408] 38. Use of the mixture according to any one of embodiments 25 to 31 as an aromatic chemical or for imparting an aromatic effect to a composition.

[0409] 39. The use according to embodiment 38, which is as a fragrance or for imparting a fragrance to a composition.

[0410] 40. A method for imparting an aromatic effect to a composition, the method comprising at least the following steps

[0411] Adding the mixture according to any one of embodiments 25 to 31 to the composition to be aromatized, or mixing the mixture according to any one of embodiments 24 to 30 with other components of the composition simultaneously or continuously, or mixing the mixture according to any one of embodiments 24 to 30 with a pre-formed mixture of a part of the other components of the composition.

[0412] 41. The use or method according to any one of embodiments 38 to 40, wherein the aromatic effect is selected from camphor note, citrus note, floral note, herbal note, ether note, fresh note, ionone note, spicy note, woody note, carrot-like note, turpentine note, pepper note, spearmint note, cedarwood note, dandelion note, earthy note, food-like note, or a combination of two or more notes.

[0413] 42. Use or method according to any one of embodiments 38 to 41, wherein the mixture of the compounds of formula (I) and (II) is used in a total amount of compounds (I) and (II) in the range of ≥ 0.001 wt.% to ≤ 70.0 wt.% based on the total weight of the composition.

[0414] Examples:

[0415] The present invention is illustrated in detail by the following non-limiting working examples. More particularly, the test methods specified below are part of the general disclosure of the present application and are not limited to the specific working examples.

[0416] Analytical methods:

[0417] NMR spectra were recorded on a Bruker DPX500 US 500 MHz spectrometer and referenced to the residual carbon resonance peak of the solvent CDCl3.

[0418] GC analysis:

[0419] GC analysis was performed using an Agilent 7890A equipped with a DB-Wax column (30 m, 0.25 mm, 0.25 μm).

[0420] Temperature program: 50 °C

[0421] 5 K / min to 220 °C

[0422] Constant flow rate: 1.0 ml / min

[0423] Carrier gas: nitrogen

[0424] Injector temperature: 220 °C

[0425] Detector temperature: 250 °C

[0426] or

[0427] GC analysis was performed using an Agilent 7890A equipped with a CP-Sil 13CB (50 m, 0.32 mm, 1.2 μm).

[0428] Temperature program: 80 °C

[0429] 10 K / min to 250 °C

[0430] Constant flow rate: 1.15 ml / min

[0431] Carrier gas: nitrogen

[0432] Injector temperature: 250 °C

[0433] Detector temperature: 280 °C

[0434] Example 1: Preparation of 3-Isopropyl-6-methylcyclohex-2-en-1-ol

[0435]

[0436] 3-Isopropyl-6-methylcyclohex-2-en-1-one (carvone; 70.0 g, purity 88%, 12% 2-hydroxy-1,4-cineole, 0.403 mol, 1.00 equivalent) was added to tetrahydrofuran (420 mL) and cooled to a temperature of 0 °C. Lithium aluminum hydride (1 M in THF, 182 g, 0.201 mol, 0.50 equivalent) was added to the mixture over 60 minutes, and the mixture was stirred at 0 °C for 2 hours. The mixture was carefully quenched with aqueous hydrochloric acid (10%, 200 mL). Additional water (150 mL) was added to dissolve the solids formed. The mixture was extracted three times with ethyl acetate (200 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. Two of these batches were combined and purified by distillation (T 头 = 51 °C, 0.1 mbar) to give the title compound (64.1 g) as a colorless liquid with a purity of 89.6 GC-a% as a mixture of isomers in a ratio of 64.48:25.07. The mixture contained approximately 10 GC-area-% of 2-hydroxy-1,4-cineole.

[0437] 1 H NMR (500 MHz, CDCl3) δ 5.50–5.20 (m, 1H), 3.95–3.57 (m, 1H), 2.58–2.31 (m, 1H), 2.14–1.72 (m, 3H), 1.69–1.13 (m, 6H), 0.97–0.76 (m, 6H).

[0438] 13 C NMR (126 MHz, CDCl3) δ 147.87, 146.26, 122.13, 120.90, 88.58, 85.74, 76.46, 73.40, 67.82, 67.78, 45.13, 37.07, 34.76, 34.48, 33.80, 32.86, 32.43, 32.01, 28.87, 26.21, 25.50, 25.47, 25.18, 21.40, 21.31, 21.07, 18.27, 18.10, 17.99, 16.30, 16.26, 14.09.

[0439] Example 2: Preparation of 5-Isopropyl-2-methylcyclohex-1-ol

[0440]

[0441] 6 g of 3-isopropyl-6-methylcyclohex-1-en-1-one (carvone, purity 87.5%, 12% 2-hydroxy-1,4-cineole) was dissolved in 100 ml of ethanol and placed in a 300 ml stainless steel autoclave. 1.8 g of Raney nickel (50% moisture) was added to the mixture. Nitrogen was introduced into the autoclave and after heating to 110 °C, hydrogen was passed through the stirred reaction mixture at a pressure of 30 bar. The mixture was hydrogenated under these conditions for 24 h.

[0442] After reduction of pressure and cooling to room temperature, the catalyst was filtered from the reaction mixture through diatomaceous earth and the solvent was evaporated. Analysis by GC (area %) showed complete conversion of carvone and a mixture of diastereoisomers in the ratio 47.3:25.8:12.8:14.0 was obtained as the product. The product mixture contained 11.6% of 2-hydroxy-1,4-cineole.

[0443] Example 3: Preparation of 5-isopropyl-2-methylcyclohex-1-ol

[0444] 81.8 g of 3-isopropyl-6-methylcyclohex-1-en-1-one (carvone, purity 97.3%) was dissolved in 80 ml of ethanol and placed in a 300 ml stainless steel autoclave. 6 g of Raney nickel (50% moisture) was added to the mixture. Nitrogen was introduced into the autoclave and after heating to 110 °C, hydrogen was passed through the stirred reaction mixture at a pressure of 30 bar. The mixture was hydrogenated under these conditions for 24 h.

[0445] After reduction of pressure and cooling to room temperature, the catalyst was filtered from the reaction mixture through diatomaceous earth and the solvent was evaporated. Analysis by GC (area %) showed complete conversion of carvone and a product with a purity of 98.4% was obtained as a mixture of diastereoisomers in the ratio 37.9:37.43:6.14:17.6.

[0446] Example 4: Preparation of 5-isopropyl-2-methylcyclohex-1-ol

[0447] 10.4 g of (S)-(+)-carvone was dissolved in 100 ml of ethanol and placed in a 300 ml stainless steel autoclave. 3 g of Raney nickel (50% moisture) was added to the mixture. Nitrogen was introduced into the autoclave and after heating to 110 °C, hydrogen was passed through the stirred reaction mixture at a pressure of 30 bar. The mixture was hydrogenated under these conditions for 24 h.

[0448] After depressurization and cooling to room temperature, the catalyst was filtered from the reaction mixture through diatomaceous earth and the solvent was evaporated. Analysis by GC (area %) showed complete conversion of carvone, and a product with a purity of 98.7% was obtained as a mixture of diastereoisomers in a ratio of 37.2:21.8:19.7:21.3.

[0449] Example 5: Preparation of 5-isopropyl-2-methylcyclohexan-1-ol

[0450] 10.2 g of (R)-(-)-carvone was dissolved in 100 ml of ethanol and placed in a 300 ml stainless steel autoclave. 3 g of Raney nickel (50% moisture) was added. Nitrogen was introduced into the autoclave and after heating to 110 °C, hydrogen was passed through the stirred reaction mixture at a pressure of 30 bar. The mixture was hydrogenated under these conditions for 24 h.

[0451] After depressurization, the catalyst was filtered from the reaction mixture through diatomaceous earth and the solvent was evaporated. Analysis by GC (area %) showed complete conversion of carvone, and a product with a purity of 99.1% was obtained as a mixture of diastereoisomers in a ratio of 36.5:21.7:19.6:22.1.

[0452] Example 6: Preparation of (5-isopropyl-2-methyl-cyclohexyl) acetate

[0453]

[0454] 5-Isopropyl-2-methyl-cyclohexanol (20.0 g, 0.128 mol, 1.00 equivalent) and N,N-dimethylpyridin-4-amine (1.25 g, 0.01 mol, 0.08 equivalent) were added to tetrahydrofuran (60 mL) and heated to 60 °C. Acetic anhydride (16.3 g, 0.160 mol, 1.25 equivalents) was added to the mixture over 30 minutes, and the mixture was stirred at 60 °C for 5 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (40 mL) and quenched with saturated aqueous NaHCO3 (200 mL). The phases were separated, the organic phase was washed with saturated aqueous NaHCO3 (20 mL) and aqueous NaCl (15 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 62 °C, 1.2 mbar) to yield the title compound (12.0 g) as a colorless liquid with a purity of 99.6 GC-a% as a mixture of isomers in a ratio of 18.09:40.21:6.31:34.96.

[0455] 11H NMR (500 MHz, CDCl3) δ 5.00–4.27 (m, 1H), 2.03–1.90 (m, 2H), 1.88–0.91 (m, 10H), 0.89–0.76 (m, 9H).

[0456] 13 13C NMR (126 MHz, CDCl3) δ 170.87, 170.81, 170.61, 170.47, 78.75, 75.61, 75.04, 73.89, 42.89, 42.67, 39.36, 37.43, 37.28, 35.31, 35.30, 34.13, 33.85, 33.18, 32.57, 32.53, 32.37, 31.09, 30.69, 30.38, 30.27, 29.17, 28.97, 28.89, 28.78, 27.60, 24.59, 22.58, 21.42, 21.38, 21.29, 21.22, 20.33, 20.23, 19.85, 19.81, 19.74, 19.73, 19.49, 18.30, 18.10, 17.13, 11.60.

[0457] Example 7: Preparation of (5-Isopropyl-2-methyl-cyclohexyl) acetate

[0458] 5 g of (S)-(+)-2-Methyl-5-isopropyl-cyclohexanol (carvacrol, 97% purity, from Example 4) was mixed with 6.9 g of acetic anhydride, 400 mg of nafion ion exchanger, and 0.9 g of acetic acid. The mixture was stirred at room temperature for 92 h.

[0459] The mixture was then filtered, and 100 ml of methyl tert-butyl ether was added. The organic solution was washed with water, and the layers were separated. The aqueous layer was extracted a second time with methyl tert-butyl ether, and then the combined organic layers were washed with saturated NaHCO3 solution. After washing with brine, the organic layer was dried over MgSO4 and the solvent was evaporated, yielding 4.3 g of the desired product with a purity of 97%, as a mixture of diastereoisomers in a ratio of 20.8:21.8:19.7:37.7.

[0460] Example 8: Preparation of (5-Isopropyl-2-methyl-cyclohexyl) acetate

[0461] 5 g of (R)-(-)-2-Methyl-5-isopropyl-cyclohexanol (carvomenthol, 99% purity, from Example 5) was mixed with 6.6 g of acetic anhydride, 400 mg of nafion ion exchanger, and 0.4 g of acetic acid. The mixture was stirred at room temperature for 69 h.

[0462] The mixture was then filtered and 100 ml of methyl tert-butyl ether was added. The organic solution was washed with water and the layers were separated. The organic layer was extracted a second time with methyl tert-butyl ether and then the combined organic layers were washed with saturated NaHCO3 solution. After washing with brine, the organic layer was dried over MgSO4, the solvent was evaporated and the crude material was distilled under vacuum to give 3.3 g of the desired product with a purity of 98.7%, as a mixture of diastereoisomers in a ratio of 13.2:2.3:22.0:43.5.

[0463] Example 9: Preparation of 3-isopropyl-6-methylcyclohex-2-en-1-yl acetate

[0464]

[0465] 3-Isopropyl-6-methylcyclohex-2-en-1-ol (13.5 g, 0.88 mol, 1.00 equivalent) and N,N-dimethylpyridin-4-amine (0.855 g, 0.007 mol, 0.08 equivalent) were mixed. Acetic anhydride (11.2 g, 0.109 mol, 1.25 equivalents) was added to the mixture over 20 minutes and the mixture was stirred at 60 °C for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (40 mL) and quenched with saturated aqueous NaHCO3 (15 mL). The phases were separated and the organic phase was washed twice with saturated aqueous NaHCO3 (15 mL) and aqueous NaCl (15 mL), dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (cyclohexane / ethyl acetate 95:5 to 90:10) to give the title compound (4.40 g) as a mixture of isomers with a purity of 97.2 GC-a% as a colourless liquid.

[0466] 1 1H NMR (500 MHz, CDCl3) δ 5.51–5.20 (m, 1H), 5.18–4.86 (m, 1H), 2.13 (dt, J = 13.8, 6.9 Hz, 1H), 2.04–1.86 (m, 4H), 1.79–1.60 (m, 2H), 1.53–1.26 (m, 2H), 1.05–0.73 (m, 9H).

[0467] 1313C NMR (126 MHz, CDCl3) δ 171.16, 170.99, 149.93, 148.58, 117.79, 117.12, 75.98, 70.84, 34.88, 34.71, 33.50, 32.16, 28.43, 26.90, 26.12, 26.03, 25.02, 21.40, 21.39, 21.24, 21.22, 21.07, 17.87, 16.24。

[0468] Example 10: Preparation of 3-ethoxy-1-isopropyl-4-methylcyclohex-1-ene

[0469]

[0470] Sodium hydride (60% dispersion in mineral oil, 3.90 g, 0.0972 mol, 1.50 equiv) was added to tetrahydrofuran (25 mL). 3-Isopropyl-6-methylcyclohex-2-en-1-ol (10.0 g, 0.0648 mol, 1.00 equiv) in tetrahydrofuran (15 mL) was added to the mixture over 15 minutes. The resulting mixture was stirred at room temperature for an additional 30 minutes. Iodoethane (24.0 g, 0.154 mol, 1.20 equiv) was added over 8 minutes. The mixture was heated to 40 °C and stirred for 5 hours. Additional iodoethane (0.50 equiv) was added and the mixture was stirred at 40 °C for an additional 18 hours. The reaction mixture was cooled to room temperature and quenched by the addition of water (25 mL). The mixture was extracted twice with 2-methoxy-2-methylpropane (30 mL). The combined organic layers were washed three times with ammonia solution (20 mL) and once with saturated NaCl solution (20 mL) and dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 975:25 to 95:5) to give the title compound (1.40 g) as a mixture of isomers with a purity of 98.2 GC-a% as a colorless liquid.

[0471] 1 1H NMR (500 MHz, CDCl3) δ 7.29–7.22 (m, 1H), 5.60–5.15 (m, 3H), 4.09–2.95 (m, 12H), 2.85–2.69 (m, 6H).

[0472] 1313C NMR (126 MHz, CDCl3) δ 146.83, 146.44, 119.49, 119.21, 80.99, 76.36, 64.37, 63.77, 34.94, 34.89, 34.01, 31.54, 28.98, 27.00, 26.62, 25.32, 24.45, 21.47, 21.40, 21.37, 21.23, 18.43, 15.87, 15.81, 14.14。

[0473] Example 11: Preparation of (5-Isopropyl-2-methyl-cyclohexyl) propionate

[0474]

[0475] 5-Isopropyl-2-methyl-cyclohexanol (20.0 g, 0.128 mol, 1.00 equivalent) and N,N-dimethylpyridin-4-amine (1.25 g, 0.01 mol, 0.08 equivalent) were added to tetrahydrofuran (60 mL) and heated to 60 °C. Propionic anhydride (20.8 g, 0.160 mol, 1.25 equivalents) was added to the mixture over 30 minutes, and the mixture was stirred at 60 °C for 5 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (40 mL) and quenched with saturated aqueous NaHCO3 (200 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (20 mL) and aqueous NaCl (15 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 84 °C, 2.5 mbar) to give the title compound (11.8 g) as a mixture of isomers in a ratio of 18.47:41.66:5.99:33.55 with a purity of 99.7 GC-a% as a colorless liquid.

[0476] 1 1H NMR (500 MHz, CDCl3) δ 5.06–4.37 (m, 1H), 2.39–2.27 (m, 2H), 2.21–0.96 (m, 12H), 0.96–0.79 (m, 9H).

[0477] 1313C NMR (126 MHz, CDCl3) δ 174.33, 174.31, 174.12, 173.97, 78.59, 75.43, 74.88, 73.69, 42.93, 42.73, 39.46, 37.52, 37.40, 35.42, 35.36, 34.16, 33.95, 33.25, 32.61, 32.58, 32.42, 31.21, 30.75, 30.43, 30.32, 29.30, 29.04, 28.85, 28.16, 28.14, 28.10, 28.04, 27.70, 24.71, 22.66, 20.38, 20.34, 19.92, 19.84, 19.80, 19.62, 18.36, 18.18, 17.20, 11.69, 9.55, 9.40, 9.35。

[0478] Example 12: Preparation of 4-Isopropyl-2-methoxy-1-methyl-cyclohexane

[0479]

[0480] Sodium hydride (60% dispersion in mineral oil, 6.14 g, 0.154 mol, 1.20 equiv) was added to tetrahydrofuran (100 mL). 5-Isopropyl-2-methyl-cyclohexanol (20.0 g, 0.128 mol, 1.00 equiv) in tetrahydrofuran (20 mL) was added to the mixture over 15 minutes. The resulting mixture was stirred at room temperature for an additional 30 minutes. Methyl iodide (21.8 g, 0.154 mol, 1.20 equiv) was added over 10 minutes. The mixture was heated to 40 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature and quenched by the addition of water (50 mL). The mixture was extracted three times with 2-methoxy-2-methylpropane (60 mL). The combined organic layers were washed three times with ammonia solution (40 mL) and once with saturated NaCl solution (40 mL) and dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 45 °C, 1.7 mbar) to give the title compound (11.0 g) as a mixture of isomers in a ratio of 18.79:6.68:40.62:33.72 with a purity of 99.7 GC-a% as a colorless liquid.

[0481] 1 1H NMR (500 MHz, CDCl3) δ 3.37–3.29 (m, 3H), 3.28–3.06 (m, 1H), 2.29–1.03 (m, 7H), 0.99–0.92 (m, 2H), 0.90–0.83 (m, 9H).

[0482] 13 13C NMR (126 MHz, CDCl3) δ 85.92, 81.98, 81.58, 80.56, 56.76, 56.52, 56.04, 55.52, 43.28, 43.03, 38.64, 38.58, 36.79, 36.73, 34.14, 33.76, 32.89, 32.84, 32.79, 32.52, 31.97, 31.18, 30.65, 30.00, 29.56, 29.33, 29.18, 29.13, 29.04, 27.36, 24.36, 23.07, 20.19, 20.12, 19.98, 19.93, 19.87, 19.82, 19.77, 18.75, 18.49, 17.34, 10.80.

[0483] Example 13: Preparation of 2-Ethoxy-4-isopropyl-1-methyl-cyclohexane

[0484]

[0485] Sodium hydride (60% dispersion in mineral oil, 6.14 g, 0.154 mol, 1.20 equiv) was added to tetrahydrofuran (100 mL). 5-Isopropyl-2-methyl-cyclohexanol (20.0 g, 0.128 mol, 1.00 equiv) in tetrahydrofuran (20 mL) was added to the mixture over 15 minutes. The resulting mixture was stirred at room temperature for an additional 30 minutes. Iodoethane (24.0 g, 0.154 mol, 1.20 equiv) was added over 10 minutes. The mixture was heated to 40 °C and stirred for 5 h. Additional iodoethane (0.50 equiv) was added and the mixture was stirred at 40 °C for an additional 18 h. The reaction mixture was cooled to room temperature and quenched by the addition of water (50 mL). The mixture was extracted three times with 2-methoxy-2-methylpropane (60 mL). The combined organic layers were washed three times with ammonia solution (40 mL) and once with saturated NaCl solution (40 mL) and dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 60 °C, 2.5 mbar) and SiO2 column chromatography (cyclohexane / ethyl acetate 95:5 to 90:10) to give the title compound (3.00 g) as a mixture of isomers in a ratio of 33.35:9.64:56.60 as a colorless liquid with a purity of 99.6 GC-a%.

[0486] 11H NMR (500 MHz, CDCl3) δ 3.88–3.08 (m, 3H), 2.25–1.02 (m, 12H), 0.98–0.80 (m, 9H).

[0487] 13 13C NMR (126 MHz, CDCl3) δ 84.32, 80.20, 79.63, 78.45, 72.42, 71.35, 64.26, 63.59, 62.82, 43.38, 43.13, 39.05, 38.67, 37.12, 36.88, 36.72, 36.59, 36.50, 35.12, 34.37, 33.77, 33.10, 32.84, 32.78, 32.60, 32.56, 30.66, 30.45, 30.37, 30.35, 30.16, 29.35, 29.26, 29.19, 29.01, 28.31, 27.75, 27.47, 24.86, 23.14, 20.56, 20.49, 20.42, 20.31, 20.03, 20.01, 19.95, 19.92, 19.91, 19.86, 19.85, 19.77, 19.76, 19.69, 18.80, 18.46, 18.46, 17.66, 15.89, 15.85, 15.82, 15.79, 10.98.

[0488] Example 14: Preparation of (4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-yl) acetate

[0489]

[0490] 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-ol (50.0 g, 0.294 mol, 1.00 equiv) and N,N-dimethylpyridin-4-amine (2.87 g, 0.023 mol, 0.08 equiv) were added to tetrahydrofuran (200 mL) and heated to 60 °C. Acetic anhydride (37.5 g, 0.367 mol, 1.25 equiv) was added to the mixture, and the mixture was stirred at 60 °C for 5 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 mL) and quenched with saturated aqueous NaHCO3 (100 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (3 x 100 mL) and aqueous NaCl (100 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头Purification was carried out at 95 °C, 1.0 mbar to give the title compound (50.4 g) as an isomer mixture with a purity of 99.9 GC-a% as a colorless liquid.

[0491] 1 H NMR (500 MHz, CDCl3) δ 4.88 (dd, J = 7.3, 2.6 Hz, 1H), 2.18 (dd, J = 13.2, 7.3 Hz, 1H), 2.13 - 2.08 (m, 1H), 2.07 (s, 3H), 1.65 - 1.43 (m, 5H), 1.39 (s, 3H), 1.02 - 0.92 (m, 6H).

[0492] 13 C NMR (126 MHz, CDCl3) δ 170.8, 88.8, 84.4, 78.4, 77.4, 77.2, 76.9, 43.3, 33.4, 32.5, 31.2, 21.2, 18.2, 17.9, 16.

[0493] Example 15: Preparation of 2-Ethoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane

[0494]

[0495] Sodium hydride (60% dispersion in mineral oil, 7.05 g, 0.176 mol, 1.50 equiv) was added to tetrahydrofuran (50 mL). 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol (20.0 g, 0.117 mol, 1.00 equiv) in tetrahydrofuran (30 mL) was added to the mixture over 15 minutes. The resulting mixture was stirred at room temperature for an additional 30 minutes. Iodoethane (27.5 g, 0.176 mol, 1.50 equiv) was added over 10 minutes. The mixture was heated to 40 °C and stirred for 23 hours. The reaction mixture was cooled to room temperature and quenched by the addition of water (50 mL). The mixture was extracted twice with 2-methoxy-2-methylpropane (60 mL). The combined organic layers were washed three times with ammonia solution (40 mL) and once with saturated NaCl solution (40 mL) and dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 86 °C - 95 °C, 2.0 mbar) and SiO2 column chromatography (cyclohexane / ethyl acetate 95:5 to 90:10) to give the title compound (7.80 g) as an isomer mixture with a purity of 99.9 GC-a% as a colorless liquid.

[0496] 11H NMR (500 MHz, CDCl3) δ 3.53 - 3.43 (m, 2H), 3.35 (dq, J = 9.3, 7.0 Hz, 1H), 2.09 (h, J = 6.9 Hz, 1H), 1.96 (dd, J = 12.5, 6.8 Hz, 1H), 1.55 (ddd, J = 8.7, 6.6, 3.0 Hz, 2H), 1.50 - 1.40 (m, 6H), 1.18 (t, J = 7.0 Hz, 3H), 0.97 (dd, J = 6.9, 2.5 Hz, 6H).

[0497] 13 13C NMR (126 MHz, CDCl3) δ 88.5, 85.4, 83.6, 64.1, 42.7, 33.9, 32.7, 31.7, 26.9, 18.3, 18.0, 16.5, 15.4.

[0498] Example 16: Preparation of 5-Isopropyl-2-methylcyclohexyl 2-methylpropanoate

[0499]

[0500] 5-Isopropyl-2-methyl-cyclohexanol (5.00 g, 0.032 mol, 1.00 eq) and N,N-dimethylpyridin-4-amine (0.313 g, 2.56 mmol, 0.08 eq) were added to tetrahydrofuran (20 mL) and heated to 60 °C. Isobutyric anhydride (6.33 g, 0.040 mol, 1.25 eq) was added to the mixture over 30 minutes, and the mixture was stirred at 60 °C for 3 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (30 mL) and quenched with saturated aqueous NaHCO3 (20 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (2 x 20 mL) and aqueous NaCl (10 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 95:5 to 90:10) to give the title compound (4.50 g) as a mixture of isomers in a ratio of 18.08:37.3:6.36:37.64 with a purity of 99.4 GC-a% as a colorless liquid.

[0501] 1 1H NMR (500 MHz, CDCl3) δ 5.03 – 4.37 (m, 1H), 2.64 – 2.43 (m, 1H), 2.20 – 1.22 (m, 9H), 1.19 – 1.13 (m, 6H), 0.96 – 0.80 (m, 9H).

[0502] 1313C NMR (126 MHz, CDCl3) δ 177.03, 176.92, 176.79, 176.69, 78.43, 75.27, 74.72, 73.53, 42.95, 42.77, 39.52, 37.58, 37.56, 35.49, 35.34, 34.69, 34.47, 34.46, 34.03, 33.86, 33.32, 32.64, 32.62, 32.45, 31.25, 30.57, 30.46, 29.45, 29.29, 29.03, 28.88, 27.77, 27.05, 24.79, 22.71, 20.43, 20.36, 19.98, 19.89, 19.85, 19.82, 19.77, 19.33, 19.31, 19.29, 19.23, 19.21, 19.17, 19.11, 18.37, 18.23, 17.20, 11.73。

[0503] Example 17: Preparation of 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-yl 2-methylpropanoate

[0504]

[0505] 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-ol (5.00 g, 0.0294 mol, 1.00 eq) and N,N-dimethylpyridin-4-amine (0.287 g, 2.35 mmol, 0.08 eq) were added to tetrahydrofuran (20 mL) and heated to 60 °C. Isobutyric anhydride (5.81 g, 0.0367 mol, 1.25 eq) was added to the mixture over 30 minutes, and the mixture was stirred at 60 °C for 3 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (30 mL) and quenched with saturated aqueous NaHCO3 (20 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (2 x 20 mL) and aqueous NaCl (10 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 90:10) to afford the title compound (4.50 g) as a mixture of isomers as a colorless liquid with a purity of >99.9 GC-a%.

[0506] 11H NMR (500 MHz, CDCl3) δ 4.84 (dd, J = 7.2, 2.6 Hz, 1H), 2.56 (p, J = 7.0 Hz, 1H), 2.11 (ddd, J = 33.3, 13.4, 7.0 Hz, 2H), 1.66–1.41 (m, 5H), 1.37 (s, 3H), 1.16 (dd, J = 8.5, 7.0 Hz, 6H), 0.96 (dd, J = 6.9, 5.1 Hz, 6H).

[0507] 13 13C NMR (126 MHz, CDCl3) δ 177.05, 88.87, 84.61, 78.11, 43.28, 34.17, 33.71, 32.57, 31.60, 19.21, 19.03, 18.26, 18.11, 16.41.

[0508] Example 18: Mixture of (5-Isopropyl-2-methyl-cyclohexyl) propionate and (4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-yl) propionate

[0509]

[0510] An approximately 85:12 GC-a% mixture of 5-Isopropyl-2-methyl-cyclohexanol and 4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol (30.0 g) and N,N-Dimethylpyridin-4-amine (1.88 g, 0.015 mol) were added to tetrahydrofuran (90 mL) and heated to 60 °C. Propionic anhydride (31.2 g, 0.240 mol) was added to the mixture over 30 minutes, and the mixture was stirred at 60 °C for 3 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (60 mL) and quenched with saturated aqueous NaHCO3 (300 mL). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (30 mL) and aqueous NaCl (20 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 72 °C, 1.5 mbar) to give the title compound (25.4 g) as a colorless liquid with a total purity > 99 GC-a% as an isomeric mixture of (5-Isopropyl-2-methyl-cyclohexyl) propionate and (4-Isopropyl-1-methyl-7-oxabicyclo[2.2.1]hept-2-yl) propionate in a ratio of 93:6 to 88:11.

[0511] Example 19: Mixture of 2-Methoxy-4-isopropyl-1-methyl-cyclohexane and 2-Methoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane

[0512]

[0513] Sodium hydride (60% dispersion in mineral oil, 9.21 g, 0.154 mol) was added to tetrahydrofuran (110 mL). An approximately 85:12 GC-a% mixture of 5-isopropyl-2-methyl-cyclohexanol and 4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptan-2-ol (30.0 g) in tetrahydrofuran (40 mL) was added to the mixture over 15 minutes. The resulting mixture was stirred for an additional 30 minutes at room temperature. Methyl iodide (32.7 g, 0.230 mol) was added over 10 minutes. The mixture was heated to 40 °C and stirred for 2 hours. The reaction mixture was cooled to room temperature and quenched by the addition of water (75 mL). The mixture was extracted three times with 2-methoxy-2-methylpropane (80 mL). The combined organic layers were washed three times with ammonia solution (60 mL), once with saturated NaCl solution (40 mL), dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by distillation (T 头 = 46 °C, 1.8 mbar) to yield the title compound (22.6 g) as a colorless liquid with a purity > 99 GC-a%, as an isomeric mixture of 2-methoxy-4-isopropyl-1-methyl-cyclohexane and 2-methoxy-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane in a ratio of 97:3 to 90:10.

[0514] Other mixtures were prepared by mixing the corresponding compounds (I) and (II) in the weight ratios indicated in Table I.

[0515] 3. Olfactory evaluation

[0516] To test the quality and intensity of the compounds of the present invention, an aroma strip test was conducted.

[0517] For this purpose, absorbent strips were soaked in a solution containing 1 to 10 wt.% of the compound to be tested in triethyl citrate. After evaporation of the solvent (approx. 30 s), the aroma effect was evaluated olfactorily by trained perfumers.

[0518] Table I:

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525] Advantageous compositions

[0526] According to Tables 2 and 3, the mixtures / compounds indicated in Table I are formulated into a composition. The mixtures / compounds from Table I are labeled as "Compound P" in Tables 2 and 3.

[0527] Table II: Compositions 1A and 1B

[0528]

[0529] Table III: Compositions 2A and 2B

[0530]

[0531] The compositions according to Table II and Table III (i.e., 1A, 1B, 2A, 2B) can be included in various compositions selected from: deodorant pump sprays, cleansing conditioners, facial wash gels, foam bath concentrates, hairsprays, self-foaming body washes, sprayable sunscreen care lotions, sprayable sunscreen protection lotions, emollient facial cleansing gels, two-phase oil foam baths, shampoos, shower gels, water-alcohol AP / deodorant pump sprays, aerosols, water / alcohol AP / deodorant roll-ons, "out-of-bed" type styling gels, shaving foams, baby shampoos for sensitive skin, body washes for sensitive skin, shine-enhancing shampoos for sensitive scalps, deodorant sticks, baby wipes, aftershave balms, facial gels, facial day care creams, facial cleansers, body lotions, sunscreen SPF50+, sprayable emulsions, hand dishwashing detergents - regular, hand dishwashing detergents - concentrates, household cleaners - concentrates, all-purpose cleaners, antibacterial fabric softeners, detergent compositions, powder detergent compositions, and liquid detergent compositions.

[0532] Those skilled in the art may be proficient in various formulations of the above products.

[0533] Compositions 1A, 1B, 2A, and 2B can be formulated, for example, in a specific formulation as disclosed in IP.com Number: IPCOM000258614D, titled New Aroma Chemicals, pages 6 to 46, Tables 1 to D13, where "Fragrance Composition 1A" is replaced by an equal amount of Composition 1A, 1B, 2A, or 2B.

Claims

1. At least one compound of formula (I) Compound of formula (I) or a stereoisomer thereof or a mixture of different stereoisomers,[[]] wherein ---- represents a single bond or a double bond, and R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group,[[]] for use as an aroma chemical.

2. Use according to claim 1, which is for imparting an aromatic effect to a composition.

3. Use according to any one of claims 1 or 2, which is as a fragrance or for imparting a fragrance to a composition.

4. Use according to any one of claims 1 to 3, wherein The compound of formula (I) is a compound of formula (Ia), Compound of formula (Ia) or a stereoisomer thereof or a mixture of different stereoisomers,[[]] wherein R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group.

5. Use according to any one of claims 1 to 3, wherein The compound of formula (I) is a compound of formula (Ib) Compound of formula (Ib) or a stereoisomer thereof or a mixture of different stereoisomers,[[]] wherein R is a straight-chain or branched C1-C6-alkyl group, a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group.

6. Use according to any one of claims 1 to 5, wherein R is a straight-chain or branched C1-C6-alkyl group, and preferably is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

7. The use according to claim 6, wherein R is methyl or ethyl.

8. Use according to any one of claims 1 to 5, wherein, R is a formyl group, or a straight-chain or branched C1-C4-alkylcarbonyl group.

9. The use according to claim 8, wherein R is a straight-chain or branched C1-C4-alkylcarbonyl group, and preferably is methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl or tert-butylcarbonyl.

10. The use according to claim 9, wherein R is a straight-chain or branched C1-C3-alkylcarbonyl group, and preferably is methylcarbonyl, ethylcarbonyl or isopropylcarbonyl, and more preferably is methylcarbonyl or ethylcarbonyl.

11. Use according to any one of claims 1 to 4 and 8 to 10, wherein The compound of formula (I) is a compound of formula (Ia) wherein R is a straight-chain or branched C1-C3-alkylcarbonyl group, preferably methylcarbonyl or ethylcarbonyl.

12. Use according to any one of claims 1 to 11, wherein The compound of formula (I) is used in admixture with: a compound of formula (II) Compound of formula (II) or a stereoisomer thereof or a mixture of different stereoisomers,[[]] wherein R is as defined in any one of claims 1 and 6 to 11; wherein preferably, R has the same meaning in the compounds of formula (I) and (II).

13. A method for imparting an aromatic effect, preferably a fragrance, to a composition, the method comprising at least the following steps: Adding at least one compound of formula (I) according to any one of claims 1 and 4 to 11 or the mixture according to claim 12 to the composition to be aromatized, or mixing at least one compound of formula (I) according to any one of claims 1 and 4 to 11 or the mixture according to claim 12 simultaneously or continuously with other components of the composition, or mixing at least one compound of formula (I) according to any one of claims 1 and 4 to 11 or the mixture according to claim 12 with a preformed mixture of a part of the other components of the composition.

14. The use or method according to any one of claims 1 to 13, wherein The aromatic effect is selected from fresh fragrance notes, mint fragrance notes, stale fragrance notes, carrot-like fragrance notes, natural fragrance notes, root fragrance notes, violet fragrance notes, powdery fragrance notes, floral fragrance notes, woody fragrance notes, warm fragrance notes, ionone fragrance notes, fruity fragrance notes, camphor fragrance notes, citrus fragrance notes, herbal fragrance notes, etheric fragrance notes, gourmand fragrance notes, anise fragrance notes, ambrettolide-like fragrance notes, animal fragrance notes, civet fragrance notes, soft fragrance notes, incense fragrance notes, musty fragrance notes, fatty fragrance notes, tobacco fragrance notes, green leaf fragrance notes, spicy fragrance notes, acid fruit fragrance notes, juniper fragrance notes, pepper fragrance notes, spearmint fragrance notes, cedarwood fragrance notes, dandelion fragrance notes, earthy fragrance notes, food-like fragrance notes, or a combination of two or more of these fragrance notes.

15. The use or method according to any one of claims 1 to 14, wherein The composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

16. The use or method according to any one of claims 1 to 15, wherein, The compound of formula (I) (if compound (II) is absent) or the mixture of compounds (I) and (II) is present in an amount in the range of ≥0.01 wt.-% to ≤70.0 wt.-% based on the total weight of the composition.

17. A compound having formula (Ia) A compound having formula (Ia) or a stereoisomer thereof or a mixture of different stereoisomers, wherein R is isopropylcarbonyl.

18. A compound having formula (Ib) A compound having formula (Ib) or a stereoisomer thereof or a mixture of different stereoisomers, wherein R is a straight-chain or branched C1-C6-alkyl, and preferably is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl or hexyl.

19. A compound having the formula (Ib) according to claim 18, wherein, R is methyl or ethyl, and preferably is ethyl.

20. A composition comprising at least one compound of formula (I) according to any one of claims 1 and 4 to 11 or the mixture according to claim 12, and (i) at least one aroma chemical (X) different from the compounds of formula (I) and (II), or (ii) at least one non-aromatic chemical carrier, or (iii) both (i) and (ii), wherein the at least one compound of formula (I) (if compound (II) is absent) or the mixture of compounds of formula (I) and (II) is preferably present in an amount in the range of ≥0.01 wt.-% to ≤70.0 wt.-% based on the total weight of the composition.

21. The composition according to claim 20, which comprises at least one compound of formula (I) according to any one of claims 1 and 4 to 11 or the mixture according to claim 12, at least one aroma chemical (X) different from the compounds of formula (I) and (II), and optionally at least one non-aromatic chemical carrier, wherein the at least one aroma chemical (X) different from the compounds of formula (I) and (II) is selected from the group consisting of geranyl acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis-isomer content of more than 60 wt.%), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, linalool, 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-indanyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indanyl acetate, citronellol, citronellyl acetate, citronellol, geraniol, tetrahydrogeraniol, vanillin, linalyl acetate, styralyl acetate, octahydro-2,3,8,8-tetramethyl-2-naphthalenone, 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-n-methylionone, α-isomethylionone, coumarin, terpinyl acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, α-amylcinnamaldehyde, ethylene brassylate, (E)-3-methylcyclopentadeca-5-enone, (Z)-3-methylcyclopentadeca-5-enone, 15-pentadecen-11-olide, 15-pentadecen-12-olide, 15-cyclopentadecanolide, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, citral, citronellal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate (preferably having 70 wt.%, or more, of cis-isomer content), 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2-tert-butylcyclohexyl) acetate, 3-[5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl]cyclohexan-1-ol, menthone, isomenthone, carvone, camphor, β-ionone, β-nor-methylionone, β-iso-methylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

22. The composition according to any one of claims 20 and 21, wherein, These non-aromatic chemical carriers are selected from the group consisting of surfactants, emollients and solvents, wherein these solvents are selected from the group consisting of: ethanol, isopropanol, propylene glycol, dipropylene glycol, 1,2-butanediol, diethylene glycol monoethyl ether, glycerol, diethyl phthalate, isopropyl myristate, triethyl citrate, and benzyl benzoate.

23. The composition according to any one of claims 20 to 22, which composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, compositions for aroma dispensers, foods, food supplements, pharmaceutical compositions, or crop protection compositions.

24. A mixture comprising at least one compound having the formula (I) Compound having the formula (I) or a stereoisomer thereof or a mixture of different stereoisomers thereof, wherein ---- represents a single bond or a double bond, and at least one compound having the formula (II) Compound having the formula (II) or a stereoisomer thereof or a mixture of different stereoisomers thereof, wherein R in compounds (I) and (II) is independently as defined in any one of claims 1 and 6 to 11; wherein in the compounds having the formula (I) and (II), R preferably has the same meaning.

25. The mixture according to claim 24, wherein, R is methyl, ethyl, methylcarbonyl, ethylcarbonyl or isopropylcarbonyl; and preferably is methylcarbonyl or ethylcarbonyl.

26. The mixture according to any one of claims 24 to 25, wherein, The weight ratio of the total amount of the compound having the formula (I) to the total amount of the compound having the formula (II) is in the range of 99.99:0.01 to 0.01:99.99, preferably 100:1 to 1:1, more preferably 50:1 to 1:1, even more preferably 35:1 to 2:1 and especially 25:1 to 3:1.

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