Substituted 1, 3-dioxolan-4-ones and 1, 3-dioxane-4-ones as perfume ingredients

Abstract

The present invention relates to the use of 1, 3-dioxolane-4-ones and 1, 3-dioxane-4-ones of formula (I) wherein R1 to R4 are as defined in the claims and the description, as aromatic ingredients. Said compounds are used to impart an aromatic effect, in particular a fragrance, to a composition, and also to enhance and / or modify the fragrance, in particular a fragrance, of a composition. The invention further relates to a method for imparting an aroma to a composition by incorporating said compounds into the composition, to a composition comprising at least one of said compounds, and to specific 1, 3-dioxolane-4-ones and 1, 3-dioxane-4-ones. # imgabs0 #

Description

Field of the Invention

[0001] The present invention relates to the use of 2-substituted 1,3-dioxolan-4-ones and 1,3-dioxan-4-ones as fragrance ingredients. The compounds are used to impart a fragrance effect, in particular a scent, to a composition and are also used to enhance and / or modify the fragrance of a composition, in particular the scent. The present invention further relates to a method for fragrancing a composition by incorporating the compounds into the composition, to a composition comprising at least one of the compounds, and to specific 1,3-dioxolan-4-ones and 1,3-dioxan-4-ones. 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 be able to meet the numerous properties desired in a very diverse range of application fields. 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, thereby contributing to the rich and interesting sensory properties of the composition, especially the olfactory properties. In this regard, aroma chemicals which can impart the following fragrance notes to a composition are of the greatest interest: camphoraceous, nutty, technical, herbaceous, tobacco, balsamic, foody, animalic, floral, fresh, herbaceous, woody, green, floral, fruity, yeasty, aniseed, reminiscent of isovaleraldehyde, waxy, powdery, alcoholic, minty, musty, aquatic, or a combination of two or more fragrance notes. In addition, substantivity and persistence are of particular interest in order to obtain a 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 odor-intensive substances with a pleasant odor. Furthermore, they should be combinable with other aroma chemicals, thus allowing the generation of novel and favorable sensory properties and can be used in a composition.

[0008] The object of the present invention is to provide aroma chemicals that have a pleasant aroma, in particular a pleasant olfactory effect; preferably selected from one or a combination of two or more of the following effects: camphor note, nut note, technical note, herb note, tobacco note, balsam note, food note, animal note, floral note, fresh note, herb note, woody note, green leaf note, floral fragrance note, fruit fragrance note, yeast note, anise note, a note reminiscent of isovaleraldehyde, wax note, powder note, wine note, mint note, musty note, aquatic note.

[0009] Another object of the present invention is to provide aroma chemicals that are non-toxic and can be obtained from readily available starting materials, thus allowing their rapid and economical manufacture. Summary of the Invention

[0010] The object of the present invention is achieved by providing compounds having the formula (I), which can be easily manufactured and have a pleasant aroma.

[0011] The present invention relates to at least one compound having the formula (I)

[0012]

[0013] or its stereoisomers for use as an aroma chemical,

[0014] wherein

[0015] R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl, or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0016] R2 is H, or a straight-chain or branched C1-C4-alkyl,

[0017] or

[0018] R1 and R2, together with the carbon atom to which they are bonded, combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0019] R3 is H, a straight-chain or branched C1-C4 alkyl group, a straight-chain C1-C4 alkyl group substituted with a C1-C2 alkylthio group, or a phenyl group,

[0020] R4 is H, or a straight-chain C1-C3 alkyl group, and

[0021] n is 0 or 1,

[0022] provided that the compound of formula (I) is not a compound in which

[0023] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0024] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0025] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0026] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0027] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0028] The present invention also relates to the use of at least one compound of formula (I), as defined above, for imparting an aromatic effect to a composition,

[0029] however, where the compound of formula (I) is not a compound in which

[0030] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0031] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0032] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0033] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0034] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0035] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0036] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0037] Another aspect of the invention claimed herein relates to the use of a compound of formula (I), as defined above, for modifying the aromatic character of a composition.

[0038] However, wherein the compound of formula (I) is not a compound wherein

[0039] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0040] -n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0041] -n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0042] -n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0043] -n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0044] -n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0045] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0046] A further aspect of the invention relates to a method of imparting an aromatic effect, in particular a fragrance, to a composition, which method comprises at least the step of adding at least one compound of formula (I), as defined above, to the composition to be aromatized.

[0047] However, wherein the compound of formula (I) is not a compound wherein

[0048] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0049] -n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0050] -n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0051] -n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0052] -n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0053] -n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0054] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl,

[0055] or mixing the at least one compound of formula (I) with the other components (constituents) of the composition simultaneously or successively, or mixing the at least one compound of formula (I) with a preformed mixture of a part of the other components (constituents) of the composition.

[0056] A further aspect of the invention claimed herein relates to a method of enhancing the aroma, in particular the fragrance, of a composition. The method comprises the step of adding at least one compound of formula (I) to a composition whose aroma is to be enhanced,

[0057] wherein the compound of formula (I) is as defined above,

[0058] However, wherein the compound of formula (I) is not a compound wherein

[0059] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0060] -n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0061] -n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0062] -n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0063] -n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0064] -n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0065] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl,

[0066] Alternatively, the at least one compound of formula (I) is mixed simultaneously or successively with the other ingredients of the composition (such as at least one other aromatic chemical different from the compound of formula (I) and / or at least one non-aromatic chemical carrier) to obtain an aromatic composition, or the at least one compound of formula (I) is mixed with a pre-formed mixture of a part of the other ingredients of the composition.

[0067] Yet another aspect of the invention relates to a method of altering the aroma of a composition. The method comprises the step of incorporating at least one compound (I), as defined above, into an aromatic composition to obtain an aroma-altered aromatic composition, for example by taking the steps mentioned above for the other methods of the invention.

[0068] However, the compound of formula (I) is not a compound in which

[0069] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0070] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0071] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0072] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0073] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0074] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0075] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0076] In another aspect, the invention relates to a composition comprising at least one compound of formula (I) as defined above, however, the compound of formula (I) is not a compound in which

[0077] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0078] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0079] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0080] - n is 0, R1 is n - propyl, R2 is H, R3 is methyl and R4 is H;

[0081] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0082] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0083] n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl,

[0084] and

[0085] a. at least one aromatic chemical (X) different from the compound of formula (I), or

[0086] b. at least one non - aromatic chemical carrier, or

[0087] c. both (i) and (ii).

[0088] In yet another aspect, the present invention relates to a compound (I)

[0089]

[0090] wherein

[0091] R1 is a straight - chain or branched C6 - C 11 - alkyl, straight - chain or branched C6 - C 11 - alkenyl or a 5 - membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0092] R2 is H or a straight - chain or branched C1 - C4 alkyl,

[0093] or

[0094] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5 - membered alicyclic ring,

[0095] R3 is H, a straight - chain or branched C1 - C4 - alkyl, a straight - chain C1 - C4 - alkyl substituted with C1 - C2 - alkylthio, or phenyl,

[0096] R4 is H or a straight - chain C1 - C3 - alkyl,

[0097] n is 0 or 1;

[0098] wherein the compound of formula (I) is not a compound wherein

[0099] - n is 0, R1 is nonyl, R2 is H, R3 is methyl and R4 is H;

[0100] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0101] - n is 0, R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H;

[0102] - n is 0, R1 is 1-propyl-hex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H;

[0103] - n is 1, R1 is n-heptyl, R2 is H, R3 is methyl and R4 is H;

[0104] - n is 1, R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0105] - n is 1, R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; and

[0106] - n is 1, R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

[0107] The present invention also relates to a compound of formula (Ia) (compound (I), where n is 0)

[0108]

[0109] where

[0110] R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl, or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0111] R2 is H or a straight-chain or branched C1-C4 alkyl,

[0112] or

[0113] R1 and R2 together with the carbon atom to which they are bonded form an unsubstituted 5-membered alicyclic ring,

[0114] R3 is H, a straight-chain or branched C1-C4-alkyl, a straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl, and

[0115] R4 is H,

[0116] where the compound of formula (Ia) is not a compound where

[0117] - R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0118] - R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0119] - R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0120] - R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0121] - R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0122] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0123] - R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl;

[0124] - R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H;

[0125] - R1 is 1-propylhex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H;

[0126] - R1 is methyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0127] - R1 is ethyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0128] - R1 is tert-butyl, R2 is H, R3 is 2-(methylthio)-ethyl and R4 is H;

[0129] - R1 is isopropyl, R2 is H, R3 is methyl and R4 is H;

[0130] - R1 is ethyl, R2 is methyl, R3 is methyl and R4 is H;

[0131] - R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H;

[0132] - R1 is tert-butyl, R2 is H, R3 is phenyl and R4 is H;

[0133] - R1 is isobutyl, R2 is H, R3 is methyl and R4 is H;

[0134] - R1 is tert-butyl, R2 is H, R3 is methyl and R4 is H;

[0135] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0136] - R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0137] - R1 is methyl, R2 is methyl, R3 is isopropyl and R4 is H;

[0138] - R1 is methyl, R2 is methyl, R3 is isobutyl and R4 is H;

[0139] - R1 is methyl, R2 is methyl, R3 is phenyl and R4 is H;

[0140] - R1 is tert - butyl, R2 is H, R3 is isopropyl and R4 is H; and

[0141] - R1 is n - pentyl, R2 is H, R3 is methyl and R4 is H.

[0142] The present invention also relates to a compound of formula (Ib) (compound (I), where n is 1)

[0143]

[0144] wherein

[0145] R1 is a straight - chain C1 - C6 alkyl group,

[0146] R2 is H, or a straight - chain C1 - C3 alkyl group,

[0147] or

[0148] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5 - membered alicyclic ring,

[0149] R3 is H, or a straight - chain C1 - C3 alkyl group,

[0150] R4 is H, or a straight - chain C1 - C3 alkyl group;

[0151] wherein the compound of formula (Ib) is not a compound wherein

[0152] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0153] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0154] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0155] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0156] - R1 is n - hexyl, R2 is H, R3 is methyl and R4 is H; and

[0157] -R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

[0158] In addition, the compounds of formula (I) can be produced in good yield and purity by a simple synthesis starting from readily available starting materials. Thus, the compounds of the invention claimed herein can be produced on a large scale and in a simple and cost-effective manner. Detailed Description

[0159] Compound (I) is generally designated as 1,3-dioxolan-4-one or 1,3-dioxan-4-one, and in some cases, in addition, it is specified that they are substituted at the 2-position (the 2-position is the carbocyclic atom carrying R1 (and R2)). However, strictly speaking, this numbering is correct only when compound (I) is monocyclic. When R1 and R2 together with the carbon atom to which they are bonded form a ring, thus giving rise to a spiro-bicyclic compound (I), the counting order changes (for example, in compound (I) in which n is 0, the oxygen ring atoms are counted as being in the 1,4-positions in this case, the oxo (=O) group is in the 2-position, and R3 / R4 are in the 3-position). However, for simplicity, all compounds (I) are referred to as 1,3-dioxolan-4-one or 1,3-dioxan-4-one, unless a specific spiro-bicyclic compound (I) is specified, which of course is named by its correct (IUPAC) name.

[0160] 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 invention claimed herein. Thus, the phrases "in one embodiment" or "in a preferred embodiment" or "in a preferred embodiment" that appear in different places throughout this specification are not necessarily all referring to the same embodiment, but may refer to the same embodiment. In addition, 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. Moreover, although some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are intended 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, any of the claimed embodiments are used in any combination in the appended claims.

[0161] In addition, the 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 in the range. To avoid doubt, the applicant is entitled to any equivalent manner in accordance with applicable law.

[0162] In the context of the present invention, the term "aroma" refers to a sensory property and includes an odor and / or a flavor. Sensory properties are related to human sensory perception.

[0163] The term "aromatic chemical" denotes a substance used to obtain a sensory or sensorial (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 "aromatic effect" or "fragrance effect" (used interchangeably herein) as used herein is related 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.

[0164] As used herein, the term "aromatic composition" refers to a composition that causes an aroma. The term aromatic composition includes an "odor composition" and / or a "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.

[0165] The term "aromatic property" denotes the overall aromatic effect of an aromatic chemical and is composed of the individual aromatic effects of the aromatic chemical.

[0166] The term odor composition includes a "fragrance composition" or an "aroma composition" (used interchangeably herein), which mainly causes an odor effect that is generally perceived as pleasant.

[0167] The general expressions "favorable sensory property" or "favorable sensorial property" describe the pleasantness and clarity of the sensorial effect conveyed by an aromatic chemical. "Pleasantness" and "clarity" are terms familiar to those skilled in the art such as perfumers. Pleasantness generally refers to a spontaneously induced, positively perceived, pleasant 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 pleasant because the odor 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 are produced after smelling the substance, in this instance thus a pleasant and clear apple odor, then the substance has particularly favorable sensory properties.

[0168] 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 considered that the two compounds need not be used in the form of a physical mixture of the compounds, but can be used separately (e.g., added). When the compounds are used separately, they can be used (e.g., added) sequentially in any order (i.e., one after another) or simultaneously (i.e., substantially at the same time).

[0169] The terms "boosting" or "boost" are used herein to describe the action of enhancing and / or altering the aroma of an aroma chemical or composition (correspondingly an aroma composition). The term "enhancing" includes an improvement in the pleasantness and / or clarity and / or intensity of the aroma. The term "altering" includes a change in the aroma properties. The terms "pleasantness" and "clarity" are familiar to those skilled in the art such as perfumers and have the corresponding meanings.

[0170] The 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 a definition of the odor effect is no longer required.

[0171] When an application characterized by a top note is desired, where the odor is to be transmitted particularly quickly and strongly, a boosting effect is particularly desired in the fragrance composition, for example in deodorants, air fresheners, or in the flavoring part of chewing gum.

[0172] The terms "the invention relates to" and "the invention is directed to" are used synonymously throughout the present invention.

[0173] The term "persistence" describes the evaporation behavior of an aroma chemical over time. Persistence can be determined, for example, by applying the aroma chemical to a test strip and subsequently subjecting the test strip to an olfactory evaluation of the odor effect. For an aroma chemical with high persistence, the time span during which the panel can still identify the aroma effect is long.

[0174] The term "fastness" describes the interaction of an aroma 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 aroma chemical and subsequently subjecting the textile (wet textile) to an olfactory evaluation directly after washing and evaluating the dry textile after long-term storage.

[0175] The term "stability" describes the behavior of an aroma chemical after contact with oxygen, light and / or other substances. An aroma chemical with high stability retains its aroma properties over a long period of time, preferably in various compositions and under various storage conditions.

[0176] In order to impart a long-lasting aroma effect to a composition or to a surface treated with a composition, the persistence, fastness and stability of the aroma chemical in the composition should preferably be high.

[0177] The term "alkyl" denotes a straight-chain or branched-chain alkyl group having in each case the specified number of carbon atoms. Examples of C1-C3-alkyl are methyl, ethyl, n-propyl and isopropyl. Examples of straight-chain C1-C3-alkyl are methyl, ethyl and n-propyl. Examples of C1-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl ( = sec-butyl), isobutyl and tert-butyl. Examples of straight-chain C1-C4-alkyl are methyl, ethyl, n-propyl and n-butyl. Examples of straight-chain C1-C6-alkyl are methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl. Examples of C1-C8-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, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl and its (other) structural isomers. In addition to those mentioned for C1-C8-alkyl, examples of C1-C 11 -alkyl are also n-nonyl, n-decyl, 2-propylheptyl, 3-propylheptyl, n-undecyl and its (other) structural isomers. C6-C 11Examples of -alkyl are 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, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, n-nonyl, n-decyl, 2-propylheptyl, 3-propylheptyl, n-undecyl and its (other) structural isomers.

[0178] Strictly speaking, the term "alkenyl" denotes a straight-chain or branched-chain aliphatic acyclic hydrocarbon group having a specified number of carbon atoms and containing a single unsaturation (i.e., one C-C double bond), where the C-C double bond can be in any position. However, as used in the present invention, the term also encompasses "alkapolyenyl", i.e., a straight-chain or branched-chain aliphatic acyclic hydrocarbon group having a specified number of carbon atoms and two or more conjugated or isolated but not cumulated C-C double bonds. C2-C in the strict sense 11Examples of -enyl (i.e., mono-unsaturated) are ethenyl (vinyl), 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, nonenyl, decenyl, undecenyl and their (other) structural isomers. C6-C 11Examples of the -enyl group are 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, nonenyl, 2,6-dimethylhept-5-en-1-yl, decenyl, undecenyl and their (other) structural isomers.

[0179] Examples of the alkyl polyenyl group are buta-1,3-dien-1-yl, buta-1,3-dien-2-yl, penta-1,3-dien-1-yl, penta-1,3-dien-2-yl, penta-1,3-dien-3-yl, penta-1,3-dien-4-yl, penta-1,3-dien-5-yl, penta-1,4-dien-1-yl, penta-1,4-dien-2-yl, penta-1,4-dien-3-yl, 2,6-dimethylhepta-1,5-dien-1-yl, (E)-2,6-dimethylhepta-1,5-dien-1-yl, (Z)-2,6-dimethylhepta-1,5-dien-1-yl, undeca-3,7,10-trien-1-yl, (3E,7E)-undeca-3,7,10-trien-1-yl, etc.

[0180] C1-C2-alkylthio is methylthio (CH3-S-) or ethylthio (CH3CH2-S-).

[0181] A straight-chain C1-C4-alkyl group substituted by a C1-C2-alkylthio group is a straight-chain C1-C4-alkyl group as defined above, wherein one hydrogen atom is replaced by a C1-C2-alkylthio group as defined above. Examples are methylthiomethyl, ethylthiomethyl, 1-(methylthio)-ethyl, 2-(methylthio)-ethyl, 1-(ethylthio)-ethyl, 2-(ethylthio)-ethyl, 1-(methylthio)-propyl, 2-(methylthio)-propyl, 3-(methylthio)-propyl, 1-(ethylthio)-propyl, 2-(ethylthio)-propyl, 3-(ethylthio)-propyl, 1-(methylthio)-butyl, 2-(methylthio)-butyl, 3-(methylthio)-butyl, 4-(methylthio)-butyl, 1-(ethylthio)-butyl, 2-(ethylthio)-butyl, 3-(ethylthio)-butyl, and 4-(ethylthio)-butyl.

[0182] A 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom may be fully or partially unsaturated. A fully unsaturated heterocycle containing an oxygen atom as a heteroatom is aromatic. Examples are 2-furyl (2-furanyl) or 3-furyl (3-furanyl). A partially unsaturated heterocycle containing an oxygen atom as a heteroatom is a dihydrofuranyl ring. Examples are 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, and 2,5-dihydrofuran-3-yl. Preferably, the 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom is heteroaromatic; i.e., it is a furanyl ring (i.e., 2- or 3-furanyl).

[0183] If R1 and R2 combine with the carbon atom to which they are bonded to form an unsubstituted 5- or 6-membered cycloaliphatic ring, this results in a cyclopentyl or cyclohexyl ring being spiro-bonded at the 2-position of the 1,3-dioxolane-4-one or 1,3-dioxane-4-one ring (the 2-position means the carbon atom carrying R1 and R2. In the correct terminology of spiro rings, this carbon atom is not counted). Alternatively expressed, R1 and R2 together form a bridging group -(CH2)4- or -(CH2)5-.

[0184] Unless otherwise specified herein, "compound (I)" as described herein refers to a compound defined by formula (I) or a salt or stereoisomer thereof.

[0185] Compounds having formula (I) include compounds represented by compounds having formula (Ia) and compounds having formula (Ib).

[0186] The term "stereoisomer" 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).

[0187] In the context of the present invention, for example, if any one of R1 to R4 contains one or more stereocenters and / or if R1 can exist as a Z- or E-isomer (i.e., if it represents an alkenyl group with the corresponding substitution pattern), then stereoisomers can exist. In addition, depending on the meaning and substitution pattern of the groups R1 to R4 on the 1,3-dioxolane-4-one or 1,3-dioxane-4-one ring, Z- or E-isomers of these rings can be formed. Specific examples of stereoisomers are compounds (I) in which R3 is a straight-chain or branched C1 - C4-alkyl, a straight-chain C1 - C4-alkyl substituted with C1 - C2-alkylthio, or phenyl, and R4 is H, and the carbon atom carrying R3 and R4 is in the S- or R-configuration.

[0188] Use :

[0189] One aspect of the present invention relates to at least one compound of formula (I)

[0190]

[0191] or its stereoisomers for use as aroma chemicals,

[0192] wherein,

[0193] R1 is a straight-chain or branched C1 - C 11 -alkyl, a straight-chain or branched C2 - C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0194] R2 is selected from H, a straight-chain or branched C1 - C4 alkyl,

[0195] or

[0196] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered cycloaliphatic ring,

[0197] R3 is selected from H, straight-chain or branched C1-C4-alkyl, straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl,

[0198] R4 is selected from H, or straight-chain C1-C3-alkyl,

[0199] n is 0 or 1,

[0200] wherein the compound of formula (I) is not a compound wherein

[0201] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0202] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0203] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0204] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0205] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0206] Examples of the use of the present invention relate to the use of at least one compound of formula (I) as defined above to impart an aromatic effect to a composition, however, wherein the compound of formula (I) is not a compound wherein

[0207] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0208] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0209] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0210] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0211] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0212] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0213] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0214] In a preferred embodiment of the use according to the invention, the compound (I) is a compound having the formula (Ia) (i.e., the compound (I) in which n is 0)

[0215]

[0216] wherein

[0217] R1 is selected from straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom;

[0218] R2 is selected from H, straight-chain or branched C1-C4 alkyl,

[0219] or

[0220] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0221] R3 is selected from H, straight-chain or branched C1-C4 alkyl, straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl, and

[0222] R4 is H or methyl.

[0223] Preferably, in the compound (Ia), R3 is H, methyl or phenyl; and R4 is H or methyl.

[0224] Preferably, in the compound (Ia),

[0225] R1 is straight-chain or branched C1-C8-alkyl or furyl (especially 2-furyl),

[0226] R2 is H or straight-chain or branched C1-C4 alkyl (especially H or straight-chain C1-C4 alkyl),

[0227] or

[0228] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered cycloalkyl ring (i.e., R1 and R2 together form a bridging group -(CH2)4- or -(CH2)5-),

[0229] R3 is H, methyl or phenyl, and

[0230] R4 is H or methyl.

[0231] In another preferred embodiment of the use according to the invention, compound (I) is a compound having the formula (Ib) (i.e., compound (I) in which n is 1).

[0232]

[0233] wherein

[0234] R1 is selected from straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom;

[0235] R2 is selected from H, straight-chain or branched C1-C4 alkyl,

[0236] or

[0237] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0238] R3 is selected from H, or straight-chain C1-C3-alkyl, and

[0239] R4 is selected from H, or straight-chain C1-C3-alkyl.

[0240] In particular, in compound (Ib),

[0241] R1 is straight-chain C1-C6-alkyl,

[0242] R2 is H, or straight-chain C1-C3-alkyl,

[0243] or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring;

[0244] R3 is selected from H, or straight-chain C1-C3-alkyl, and

[0245] R4 is selected from H, or straight-chain C1-C3-alkyl.

[0246] Preferably, in compound (Ib), R3 is methyl and R4 is H.

[0247] In an embodiment, the present invention relates to the use of the following compounds represented by compounds having the formula (Ia) as aroma chemicals or for imparting an aromatic effect to a composition:

[0248]

[0249]

[0250]

[0251]

[0252] More preferably, the compound having the formula (Ia) is selected from the following compounds:

[0253] - Compound (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0254] - Compound (Ia) wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0255] - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0256] - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is phenyl and R4 is H;

[0257] - Compound (Ia) wherein R1 is n-butyl, R2 is n-butyl, R3 is methyl and R4 is H;

[0258] - Compound (Ia) wherein R1 is isopropyl, R2 is H, R3 is methyl and R4 is H;

[0259] - Compound (Ia) wherein R1 is isobutyl, R2 is H, R3 is methyl and R4 is H;

[0260] - Compound (Ia) wherein R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H;

[0261] - Compound (Ia) wherein R1 is n-hexyl, R2 is H, R3 is H and R4 is H;

[0262] - Compound (Ia) wherein R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H;

[0263] - Compound (Ia) wherein R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H;

[0264] - Compound (Ia) wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0265] - Compound (Ia) wherein R1 is furan-2-yl, R2 is H, R3 is methyl and R4 is H;

[0266] - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0267] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is methyl;

[0268] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is phenyl and R4 is H;

[0269] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and - mixtures thereof.

[0270] Even more preferably, the compound of formula (Ia) is selected from the following compounds:

[0271] - Compound (Ia), wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0272] - Compound (Ia), wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0273] - Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0274] - Compound (Ia), wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0275] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0276] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and - mixtures thereof.

[0277] Particularly preferably, the compound of formula (Ia) is selected from the following compounds:

[0278] - Compound (Ia), wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0279] - Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0280] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0281] - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and

[0282] - mixtures thereof.

[0283] Specifically, the compound of formula (Ia) is a compound of formula (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H. In a specific embodiment, the compound of formula (Ia) (wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H) exists in the form of a stereoisomer selected from (5S)-2-tert-butyl-2,5-dimethyl-1,3-dioxolan-4-one or (5R)-2-tert-butyl-2,5-dimethyl-1,3-dioxolan-4-one.

[0284] In another specific embodiment, the compound (Ia) (wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H) exists in the form of a stereoisomer selected from (3S)-3-methyl-1,4-dioxaspiro[4.4]nonan-2-one or (3R)-3-methyl-1,4-dioxaspiro[4.4]nonan-2-one.

[0285] In an embodiment, the present invention relates to the use of the following compounds represented by the compounds of formula (Ib) as aroma chemicals or for imparting an aromatic effect to a composition:

[0286]

[0287]

[0288] Compound (I) can be obtained by standard methods of organic chemistry, generally by condensation of a hydroxycarboxylic acid of formula OH-C(R3)(R4)-(CH2) n -C(O)OH (wherein R3, R4 and n are as defined above) with a carbonyl compound (ketone or aldehyde) of formula R1-C(=O)-R2 (wherein R1 and R2 are as defined above). The reaction is generally carried out in the presence of a catalyst suitable for the condensation reaction (such as an inorganic acid, for example sulfuric acid, sulfamic acid, hydrochloric acid or phosphoric acid) or an acidic ion exchanger, or an organic sulfonic acid (such as methanesulfonic acid or p-toluenesulfonic acid). The individual reaction conditions for preparing the compounds of general formula (I) are well known to those skilled in the art.

[0289] Preferred embodiments of the invention claimed herein relate to the use of at least one compound of formula (I) as an aroma chemical for imparting to a composition an aroma effect selected from the group consisting of: camphoraceous note, nutty note, technical note, herbal note, tobacco note, balsamic note, food note, animal note, aromatic note, fresh note, herbal note, woody note, green note, floral note, fruity note, yeast note, anise note, a note reminiscent of isovaleraldehyde, wax note, powdery note, wine note, mint note, musty note, aquatic note, or a combination of two or more notes.

[0290] In a further embodiment, the invention claimed herein relates to the use of at least one compound of formula (I), at least one compound of formula (Ia), or at least one compound of formula (Ib) for enhancing the aroma of a composition.

[0291] In an embodiment of the invention claimed herein, at least one compound of formula (I), at least one compound of formula (Ia), or at least one compound of formula (Ib) is used as an ingredient in a perfume or fragrance composition.

[0292] In particular, at least one compound of formula (I), at least one compound of formula (Ia), or at least one compound of formula (Ib) is used to impart to a composition a note selected from the group consisting of: camphoraceous note, nutty note, technical note, herbal note, tobacco note, balsamic note, food note, animal note, aromatic note, fresh note, herbal note, woody note, green note, floral note, fruity note, yeast note, anise note, a note reminiscent of isovaleraldehyde, wax note, powdery note, wine note, mint note, musty note, aquatic note, or a combination of two or more notes.

[0293] Preferably, at least one compound of formula (I), at least one compound of formula (Ia), or at least one compound of formula (Ib) is used to impart a combination of two or more of the following effects: camphoraceous note, nutty note, technical note, herbal note, tobacco note, balsamic note, food note, animal note, aromatic note, fresh note, herbal note, woody note, green note, floral note, fruity note, yeast note, anise note, a note reminiscent of isovaleraldehyde, wax note, powdery note, wine note, mint note, musty note, aquatic note.

[0294] 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.

[0295] Preferably, the compounds of formula (I) according to the invention claimed herein are used in compositions selected from the following: 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.

[0296] Further details of the compositions are given below.

[0297] The above preferred embodiments are similarly applicable to the methods of the present invention.

[0298] Compound :

[0299] One embodiment of the invention relates to a compound of formula (I)

[0300]

[0301] or a stereoisomer thereof,

[0302] wherein

[0303] R1 is selected from straight-chain or branched C6-C 11 -alkyl, straight-chain or branched C6-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0304] R2 is selected from H, straight-chain or branched C1-C4-alkyl,

[0305] or

[0306] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring,

[0307] R3 is selected from H, straight-chain or branched C1-C4-alkyl, straight-chain C1-C4 alkyl substituted with C1-C2-alkylthio, or phenyl,

[0308] R4 is selected from H, or straight-chain C1-C3-alkyl, and

[0309] n is 0 or 1;

[0310] wherein the compound of formula (I) is not a compound wherein

[0311] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0312] -n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0313] - n is 0, R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H;

[0314] - n is 0, R1 is 1-propylhex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H;

[0315] - n is 0, R1 is n-hexyl, R2 is H, R3 is H and R4 is H;

[0316] - n is 0, R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H;

[0317] - n is 0, R1 and R2 together form -(CH2)4-, R3 is methyl and R4 is methyl;

[0318] - n is 1, R1 is n-heptyl, R2 is H, R3 is methyl and R4 is H;

[0319] - n is 1, R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0320] - n is 1, R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; and

[0321] n is 1, R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

[0322] Another embodiment of the present invention relates to a compound having the formula (Ia),

[0323]

[0324] wherein

[0325] R1 is selected from linear or branched C1-C 11 - alkyl, linear or branched C2-C 11 - alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0326] R2 is selected from H, linear or branched C1-C4-alkyl,

[0327] or

[0328] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring,

[0329] R3 is selected from H, linear or branched C1-C4-alkyl, linear C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl, and

[0330] R4 is H or methyl;

[0331] wherein the compound of formula (Ia) is not a compound wherein

[0332] - R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0333] - R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0334] - R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0335] - R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0336] - R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0337] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0338] - R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl;

[0339] - R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H;

[0340] - R1 is 1-propyl-hex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H;

[0341] - R1 is methyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0342] - R1 is ethyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0343] - R1 is tert-butyl, R2 is H, R3 is 2-(methylthio)-ethyl and R4 is H;

[0344] - R1 is isopropyl, R2 is H, R3 is methyl and R4 is H;

[0345] - R1 is ethyl, R2 is methyl, R3 is methyl and R4 is H;

[0346] - R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H;

[0347] - R1 is tert-butyl, R2 is H, R3 is phenyl and R4 is H;

[0348] - R1 is isobutyl, R2 is H, R3 is methyl and R4 is H;

[0349] - R1 is tert-butyl, R2 is H, R3 is methyl and R4 is H;

[0350] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0351] - R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0352] - R1 is methyl, R2 is methyl, R3 is isopropyl and R4 is H;

[0353] - R1 is methyl, R2 is methyl, R3 is isobutyl and R4 is H;

[0354] - R1 is methyl, R2 is methyl, R3 is phenyl and R4 is H;

[0355] - R1 is tert-butyl, R2 is H, R3 is isopropyl and R4 is H;

[0356] - R1 is n-pentyl, R2 is H, R3 is methyl and R4 is H;

[0357] - R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H; and

[0358] - R1 and R2 together form -(CH2)4-, R3 is methyl and R4 is methyl.

[0359] Another embodiment of the present invention relates to a compound having the formula (Ib),

[0360]

[0361] wherein

[0362] R1 is a straight-chain C1-C6 alkyl group,

[0363] R2 is H, or a C1-C3 alkyl group,

[0364] or R1 and R2 combine to form an unsubstituted 5-membered alicyclic ring,

[0365] R3 is selected from H, or a straight-chain C1-C3 alkyl group,

[0366] R4 is selected from H, or a straight-chain C1-C3 alkyl group;

[0367] wherein the compound having the formula (Ib) is not a compound wherein

[0368] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0369] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0370] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0371] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0372] - R1 is n - hexyl, R2 is H, R3 is methyl and R4 is H; and

[0373] - R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

[0374] In a more preferred embodiment, the present invention relates to the following compounds represented by the compound of formula (Ia):

[0375]

[0376]

[0377] Even more preferably, the compound (Ia) is selected from the following compounds:

[0378] - The compound (Ia), wherein R1 is n - butyl, R2 is n - butyl, R3 is methyl and R4 is H (Structure No. 1 in the above table); - The compound (Ia), wherein R1 is n - hexyl, R2 is H, R3 is H and R4 is H (Structure No. 5 in the above table);

[0379] - The compound (Ia), wherein R1 is n - hexyl, R2 is H, R3 is methyl and R4 is H (Structure No. 3 in the above table);

[0380] - The compound (Ia), wherein R1 is n - octyl, R2 is H, R3 is methyl and R4 is H (Structure No. 4 in the above table);

[0381] - The compound (Ia), wherein R1 is furan - 2 - yl, R2 is H, R3 is methyl and R4 is H (Structure No. 2 in the above table); and

[0382] - A mixture thereof.

[0383] Specifically, the compound (Ia) is the compound (Ia) wherein R1 is n - octyl, R2 is H, R3 is methyl and R4 is H.

[0384] In another more preferred embodiment, the present invention relates to the following compounds represented by the compound of formula (Ib):

[0385]

[0386] As explained above, the compound (I) can be obtained by standard methods of organic chemistry, generally by condensation of a hydroxycarboxylic acid having the formula OH-C(R3)(R4)-(CH2) n -C(O)OH (wherein R3, R4 and n are as defined above) with a carbonyl compound (ketone or aldehyde) having the formula R1-C(=O)-R2 (wherein R1 and R2 are as defined above). The reaction is generally carried out in the presence of a catalyst suitable for the condensation reaction (such as an inorganic acid, for example sulfuric acid, sulfamic acid, hydrochloric acid or phosphoric acid) or an acidic ion exchanger, or an organic sulfonic acid (such as methanesulfonic acid or p-toluenesulfonic acid). The individual reaction conditions for preparing the compounds of general formula (I) are well known to those skilled in the art.

[0387] Composition :

[0388] In an embodiment, the invention claimed herein relates to a composition comprising: at least one compound having the formula (I) and

[0389] (i) at least one aromatic chemical (X) different from: at least one compound having the formula (I), at least one compound having the formula (Ia), or at least one compound having the formula (Ib), or

[0390] (ii) at least one non-aromatic chemical carrier, or

[0391] (iii) both (i) and (ii);

[0392] wherein the compound having the formula (I) is not a compound wherein

[0393] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0394] -n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0395] -n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0396] -n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0397] -n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0398] -n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0399] -n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0400] Preferably, in this embodiment, the composition comprises a total amount of the compound of formula (I) in the range of ≥ 0.01 wt.% to ≤ 70.0 wt.%, based on the total weight of the composition.

[0401] Preferably, the composition is an aromatic composition, more preferably a fragrance composition.

[0402] Aromatic chemicals different from the compound of formula (I).

[0403] For the purposes of the present invention, the compound of formula (I) includes the compound of formula (Ia) and the compound of formula (Ib).

[0404] In a preferred embodiment, the composition comprises at least one aromatic chemical different from the at least one compound of formula (I). The aromatic chemical different from the compound of formula (I) is also referred to as aromatic chemical (X).

[0405] Due to its physical properties, the compound of formula (I) can be well combined with aromatic chemicals different from the compound of formula (I) and other conventional ingredients 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 promoter effect for other aromatic chemicals such as fragrances.

[0406] The aromatic chemical (X) is preferably selected from:

[0407] 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-cyclohexene-1-carboxaldehyde, 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-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)propanal, ethyl 2-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.

[0408] In a preferred embodiment, the at least one aroma chemical (X) is selected from methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, or methyl benzoate.

[0409] In another preferred embodiment, the at least one aroma chemical (X) is selected from ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol), or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0410] Additional aroma chemicals with which the compound of formula (I) can be combined to obtain the compositions of the invention claimed herein can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Volumes I and II, Montclair, NJ, 1969, self-published or H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2016. Specifically, mention may be made of:

[0411] Extracts from natural raw materials such as essential oils, concretes, absolutes, resins, balsams, oleoresins, tinctures, such as

[0412] Ambergris tincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise seed oil; Valerian oil; Basil oil; Moss absolute; Bay oil; Artemisia oil; Benzoin resin; Bergamot oil; Beeswax absolute; Birch tar; Bitter almond oil; Savory oil; Buchu leaf oil; Kahlua oil; Juniper oil; Calamus oil; Camphor oil; Cananga oil; Cardamom oil; Caraway oil; Cinnamon oil; Cinnamon absolute; Castoreum absolute; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronella oil; Lemon oil; Copaiba balsam; Copaiba balsam oil; Coriander oil; Costus root oil; Kumin oil; Cypress oil; Davana oil; Dill leaf Oil; Dill Seed Oil; Eau de Toilette Absolute; Oakmoss Absolute; Elemi Resin Oil; Tarragon Oil; Lemon Eucalyptus Oil; Eucalyptus Oil; Anise Oil; Pine Needle Oil; Galbanum Oil; Galbanum Resin; Geranium Oil; Grapefruit Oil; Guaiac Wood Oil; Guaiac Balsam; Guaiac Balsam Oil; Helichrysum Absolute; Helichrysum Oil; Ginger Oil; Orris Root Absolute; Orris Root Oil; Jasmine Absolute; Calamus Oil; Blue Chamomile Oil; Roman Chamomile Oil; Carrot Seed Oil; Quinoa Oil; Pine Needle Oil; Spearmint Oil; Caraway Oil; Lavender Oil; Lavender Absolute; Lavender Oil; Lavender Absolute; Lavender oil; lemongrass oil; lovage oil; distilled lime oil; pressed lime oil; linalool oil; litsea cubeba oil; bay leaf oil; nutmeg oil; marjoram oil; mandarin oil; cassia bark 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; red myrrh 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; mint oil; pepper oil; glycerin Pepper oil; pine oil; mint oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; broadleaf lavender oil; anise oil; styrax oil; marigold oil; fir oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka bean absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; lees oil; wormwood oil; wintergreen oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof, or components isolated therefrom;

[0413] Various flavors from the following group: hydrocarbons, such as, for example, 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; aurantium; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;

[0414] 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;

[0415] 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;

[0416] Aliphatic sulfur-containing compounds, such as 3-(methylthio)hexanol; 3-(methylthio)hexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-(acetylthio)hexyl acetate; 1-menthene-8-thiol;

[0417] Aliphatic nitriles, such as 2-nonenitrile; 2-undecenenitrile; 2-tridecenenitrile; 3,12-tridecadienenitrile; 3,7-dimethyl-2,6-octadienenitrile; 3,7-dimethyl-6-octenenitrile;

[0418] 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;

[0419] Acyclic terpene alcohols, such as geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatriene-3-ol; 2,6-dimethyl-2,5,7-octatriene-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0420] Acyclic terpene aldehydes and ketones, such as geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and dimethyl and diethyl acetals of geranial, neral and 7-hydroxy-3,7-dimethyloctanal; cyclic terpene alcohols, such as menthol; isopulegol; α-terpineol; terpinene-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nobol; cedrol; ambreinolide; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0421] Cyclic terpenoid 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);

[0422] 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;

[0423] 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;

[0424] 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;

[0425] 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-cyclopentadecanone; 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;

[0426] 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;

[0427] 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-naphthyl methyl ketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;

[0428] 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;

[0429] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

[0430] 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 - carboxylate; ethyl 2,3,6,6 - tetramethyl - 2 - cyclohexene - carboxylate; ethyl 2 - methyl - 1,3 - dioxolane - 2 - acetate;

[0431] Aryl - aliphatic alcohols, such as benzyl alcohol; 1 - phenylethanol, 2 - phenylethanol, 3 - phenylpropanol; 2 - phenylpropanol; 2 - phenoxyethanol; 2,2 - dimethyl - 3 - phenylpropanol; 2,2 - dimethyl - 3 - (3 - methylphenyl)propanol; 1,1 - dimethyl - 2 - phenylethanol; 1,1 - dimethyl - 3 - phenylpropanol; 1 - ethyl - 1 - methyl - 3 - phenylpropanol; 2 - methyl - 5 - phenylpentanol; 3 - methyl - 5 - phenylpentanol; 3 - phenyl - 2 - propen - 1 - ol; 4 - methoxy - benzyl alcohol; 1 - (4 - isopropylphenyl)ethanol;

[0432] 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;

[0433] 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;

[0434] 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;

[0435] 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-benzofuranylethanone); benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2'-naphthyl ethyl ketone;

[0436] 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;

[0437] 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 bases 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;

[0438] 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;

[0439] 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;

[0440] 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.

[0441] The aroma chemicals (X) used in the composition are obtained from known commercial sources and are purchased from Germany.

[0442] In a preferred embodiment, the composition comprises at least one compound having the formula (I) and at least one aroma chemical (X).

[0443] In a preferred embodiment, the composition comprises at least one compound having the formula (I), at least one aromatic chemical (X), and optionally at least one non-aromatic chemical carrier, wherein the at least one aromatic chemical (X) 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-iso-methylionone, 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 of the 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.

[0444] Non-aromatic chemical carrier:

[0445] The non-aromatic chemical carrier in the composition of the present invention is preferably selected from surfactants, oil component antioxidants, deodorant activators, and solvents.

[0446] 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 fix the compound of formula (I) as defined above and optionally the at least one aromatic chemical (X) (if included in the composition).

[0447] The non-aromatic chemical carrier in the composition of the present invention is preferably selected from surfactants, oil components, solvents, or any mixture of two or more of the foregoing.

[0448] Solvent

[0449] In the context of the invention claimed herein, a "solvent" is used to dilute the compound of formula (I) used according to the present invention and does not have its own aroma.

[0450] The amount of one or more solvents is adjusted according to the composition and represents a routine task for those skilled in the art.

[0451] 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.

[0452] 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.

[0453] 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.

[0454] In a preferred embodiment, the composition comprises a compound of formula (I) and at least one solvent and optionally at least one aromatic chemical (X).

[0455] Oil component

[0456] Preferably, the total oil component is present in an amount of from 0.1 wt.% to 80 wt.%, more preferably from 0.5 wt.% to 70 wt.%, still more preferably from 1 wt.% to 60 wt.%, even more preferably from 1 wt.% to 50 wt.%, particularly from 1 wt.% to 40 wt.%, more particularly from 5 wt.% to 25 wt.% and specifically from 5 wt.% to 15 wt.%, based on the total weight of the composition.

[0457] 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, cetyl myristate, stearyl myristate, isostearyl myristate, oleyl myristate, behenyl myristate, erucyl myristate, myristyl cetylate, cetyl cetylate, stearyl cetylate, isostearyl cetylate, oleyl cetylate, behenyl cetylate, erucyl cetylate, myristyl stearate, cetyl stearate, stearyl stearate, isostearyl stearate, oleyl stearate, behenyl stearate, erucyl stearate, myristyl isostearate, cetyl isostearate, stearyl isostearate, isostearyl isostearate, oleyl isostearate, behenyl isostearate, oleyl isostearate, myristyl oleate, cetyl oleate, stearyl oleate, isostearyl oleate, oleyl oleate, behenyl oleate, erucyl oleate, myristyl behenate, cetyl behenate, stearyl behenate, isostearyl behenate, oleyl behenate, behenyl behenate, erucyl behenate, myristyl erucate, cetyl erucate, stearyl erucate, isostearyl erucate, oleyl erucate, behenyl erucate 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.

[0458] In a preferred embodiment, the composition comprises at least one compound of formula (I) and at least one oil component and optionally at least one fragrance chemical (X).

[0459] Antioxidant

[0460] 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.

[0461] In a preferred embodiment, the antioxidant is selected from

[0462] · Amino acids (such as glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives,

[0463] · Imidazoles (such as urocanic acid) and their derivatives,

[0464] · Peptides, such as D,L-carnosine, D-carnosine, L-carnosine (= β-alanyl-L-histidine) and their derivatives,

[0465] · Carotenoids, carotenes (such as α-carotene, β-carotene, lycopene, lutein) or their derivatives,

[0466] · Chlorogenic acid and its derivatives,

[0467] · Lipoic acid and its derivatives (such as dihydrolipoic acid),

[0468] · 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,

[0469] · Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

[0470] · Sulfoximine compounds (such as buthionine sulfoximine, homocysteine sulfoximine, buthionine sulfone, penta-, hexa-, heptathionine sulfoximine),

[0471] · (Metal) chelating agents (such as α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

[0472] · α-Hydroxy acids (such as citric acid, lactic acid, malic acid),

[0473] · Humic acids, bile acids, bile extracts, bilirubin, biliverdin, boldine (= alkaloid from the plant Boldo tree), Boldo extract,

[0474] · EDTA, EGTA and their derivatives,

[0475] · Unsaturated fatty acids and their derivatives (such as gamma-linolenic acid, linoleic acid, oleic acid),

[0476] · Folic acid and its derivatives,

[0477] · Ubiquinone and ubiquinol and their derivatives,

[0478] · Vitamin C and derivatives (such as ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

[0479] · Tocopherol and derivatives (such as vitamin E acetate),

[0480] · Vitamin A and derivatives (such as vitamin A palmitate),

[0481] · Coniferyl benzoate of benzoin, rutic acid and its derivatives, alpha-glycosylrutin, ferulic acid, furoylglucitol,

[0482] · Butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA),

[0483] · Nordihydroguaiaretic acid, nordihydroguaiaretic acid, trihydroxybenzophenone, uric acid and its derivatives, mannose and its derivatives,

[0484] · Superoxide dismutase,

[0485] · Zinc and its derivatives (such as ZnO, ZnSO4),

[0486] · Selenium and its derivatives (such as selenomethionine),

[0487] · Stilbene and its derivatives (such as, oxyresveratrol, trans-oxyresveratrol),

[0488] or a mixture of two or more of the foregoing.

[0489] 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.

[0490] Preferably, the composition according to the invention claimed herein comprises an antioxidant in a total amount of from 0.001 wt.-% to 25 wt.-%, preferably from 0.005 wt.-% to 10 wt.-%, more preferably from 0.01 wt.-% to 8 wt.-%, still more preferably from 0.025 wt.-% to 7 wt.-%, even more preferably from 0.05 wt.-% to 5 wt.-% based on the total weight of the composition.

[0491] In a preferred embodiment, the composition comprises at least one compound having formula (I) and at least one antioxidant and optionally at least one aromatic chemical (X).

[0492] Deodorant active agent

[0493] 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.

[0494] Preferably, the deodorant active agent is selected from antiperspirants, esterase inhibitors, antibacterial agents, or a mixture of two or more of the foregoing.

[0495] 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 aluminum trichlorohydrate, zirconium aluminum tetrachlorohydrate, zirconium aluminum pentachlorohydrate and their complex compounds (e.g., with amino acids such as glycine). Aluminum chlorohydrate, zirconium aluminum tetrachlorohydrate, zirconium aluminum pentachlorohydrate, or their complex compounds are preferably used.

[0496] Preferably, the antiperspirant is selected from aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxy allantoin, aluminum chloride tartrate, zirconium aluminum trichlorohydrate, zirconium aluminum tetrachlorohydrate, zirconium aluminum pentachlorohydrate, or a mixture of two or more of the foregoing.

[0497] 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 odor in the process. Suitable esterase inhibitors are, for example, trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate. Esterase inhibitors inhibit enzyme activity 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.

[0498] 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.

[0499] Preferably, the composition according to the invention claimed herein comprises an esterase inhibitor in a total amount in the range of from 0.01 wt.-% to 20 wt.-%, preferably from 0.1 wt.-% to 10 wt.-% and more particularly from 0.5 wt.-% to 5 wt.-%, based on the total weight of the composition.

[0500] As used herein, the term "antimicrobial agent" encompasses substances having bactericidal and / or bacteriostatic properties. Typically, these substances act against 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, glyceryl monocaprate, glyceryl monocaprylate, glyceryl monolaurate (GML), diglyceryl monocaprate (DMC), salicylic acid-N-alkylamides such as salicylic acid-n-octylamide or salicylic acid-n-decylamide.

[0501] 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, glyceryl monocaprate, glyceryl monocaprylate, glyceryl monolaurate (GML), diglyceryl monocaprate (DMC), salicylic acid-N-alkylamides, or a mixture of two or more of the foregoing.

[0502] Preferably, the composition according to the invention to be protected herein comprises one or more antibacterial agents in a total amount in the range of from 0.01 wt.% to 5 wt.%, preferably from 0.1 wt.% to 2 wt.%, based on the total weight of the composition.

[0503] In a preferred embodiment, the composition comprises at least one compound having the formula (I) and at least one deodorant active agent and optionally at least one perfume chemical (X).

[0504] Surfactant

[0505] 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.

[0506] 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 wt.% to 15 wt.%, and especially from 0.1 wt.% to 10 wt.%, based on the total weight of the composition.

[0507] Preferred nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed 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 polyglycol ether chains, they can have a conventional homolog distribution, but they preferably have a narrow range of homolog distribution.

[0508] 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.

[0509] Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethylglycine ammonium, for example, cocoalkyl dimethylglycine ammonium, N-acylaminopropyl-N,N-dimethylglycine ammonium, for example, cocoacylaminopropyl dimethylglycine ammonium, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazoline, which contain 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. The fatty acid amide derivative known under the CTFA name of cocoamidopropyl betaine is particularly preferred.

[0510] 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 internal salts. Examples of suitable amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, which contain about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-coconut alkylaminopropionates, coconut acylaminoethylaminopropionates and acylsarcosines.

[0511] 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. In particular, they are alkyl sulfates, alkyl ether sulfates, alkyl ether carboxylates, acyl hydroxyethyl sulfonates, acyl sarcosinates, acyl taurines and sulfosuccinates containing straight-chain C12-C18 alkyl or acyl groups and acyl glutamates in the form of their alkali metal, ammonium or alkanolammonium salts.

[0512] 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. "Esterquats" are generally understood to be quaternized fatty acid triethanolamine ester salts. They can impart a particular 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.

[0513] 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 impart 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: camphoraceous, nutty, technical, herbaceous, tobacco, balsamic, foody, animalic, floral, fresh, herbaceous, woody, green, floral, fruity, yeasty, aniseed, an odor reminiscent of isovaleraldehyde, waxy, powdery, winey, minty, musty, aquatic, or a combination of two or more fragrance notes.

[0514] In a preferred embodiment, the composition comprises at least one compound of formula (I) and at least one surfactant and optionally at least one aroma chemical (X).

[0515] 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.

[0516] Perfume compositions can be selected from fine fragrances, air fresheners in liquid form, gel form or applied to a solid carrier, aerosol sprays, scented detergents, perfume candles, or oils such as lamp oil or massage oils.

[0517] Examples of fine fragrances are perfume extracts, eau de parfum, eau de toilette, eau de cologne, solid perfumes and eau de parfum concentrée.

[0518] 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, oil-in-water, water-in-oil and water-in-oil-in-water make-up 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 straightening 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 mascara; and products for oral and dental hygiene such as toothpaste, dental floss, mouthwash, breath fresheners, dental foams, dental gels and dental strips.

[0519] Hygiene products may be selected from incense sticks, insecticides, repellents, propellants, rust removers, aromatic freshening wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, handkerchief tissues, dishwashing agents and deodorants.

[0520] Cleaning compositions such as cleaners 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 purposes, bath and hygiene cleaners, scrubbing milks, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polish, floor wax, shoe polish, disinfectants, surface disinfectants and hygiene cleaners, brake cleaners, pipe cleaners, scale removers, grill and oven cleaners, algae and moss removers, mold removers, facade cleaners.

[0521] 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.

[0522] 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.

[0523] 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, ingredients, or extracts. Food supplements can be seen in various forms such as tablets, capsules, soft gels, soft capsules, liquids, or powders.

[0524] 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.

[0525] 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.

[0526] Preferably, the composition according to the present invention further comprises at least one adjuvant selected from the following: 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, substances for preventing foaming, foam promoters, fungicides, gelling agents, gel-forming agents, hair care agents, hair styling agents, hair smoothing agents, water-increasers, moisturizing substances, wetting substances, bleaching agents, enhancers, detergents, optical brighteners, impregnating agents, anti-fouling agents, friction reducers, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, covering agents, polishing agents, luminescent agents, polymers, powders, proteins, fatliquoring agents, stripping agents, silicones, skin soothers, skin cleansing agents, skin care agents, skin healing agents, skin brighteners, skin protectors, skin softeners, coolants, skin coolants, warmers, skin warmers, 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.

[0527] A method for preparing a composition and imparting an aromatic effect to the composition.

[0528] One embodiment of the present invention relates to a method for preparing a composition for at least one compound having formula (I), the composition comprising:

[0529] (i) At least one aromatic chemical (X) other than the compounds according to the invention or

[0530] (ii) At least one non-aromatic chemical carrier, or

[0531] both (i) and (ii).

[0532] The present invention also relates to a method for enhancing the aromatic effect of a composition, which method comprises incorporating at least one compound of formula (I) into the composition.

[0533] 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, which comprises incorporating at least one compound of formula (I) into 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.

[0534] 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 camphor note, a nut note, a technical note, a herbaceous note, a tobacco note, a balsamic note, a food note, an animal note, an aromatic note, a fresh note, a herbaceous note, a woody note, a green note, a floral note, a fruity note, a yeast note, an anise note, a note reminiscent of isovaleraldehyde, a wax note, a powdery note, a wine note, a mint note, a musty note, an aquatic note, or a combination of two or more elements, which method comprises incorporating at least one compound of formula (I) into 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.

[0535] amount

[0536] Generally, the total amount of the compound of formula (I) in the compositions, methods and uses according to the invention is typically adapted to the particular intended use or application and can thus vary within a wide range. Generally, conventional standard commercial amounts for aromatic chemicals, preferably for fragrances, are used.

[0537] Preferably, the composition according to the invention comprises from 0.001 wt.% to 99.9 wt.% of the total amount of the compound of formula (I) based on the total weight of the composition.

[0538] In particular, the composition comprises a compound of formula (I) in an amount of from 0.001 wt.% to 99.5 wt.%, preferably from 50 wt.% to 99 wt.%, more preferably from 80 wt.% to 95 wt.%, and especially from 90 wt.% to 95 wt.%, based on the total weight of the composition.

[0539] In particular, the composition comprises a compound of formula (I) in an amount of from 0.005 wt.% to 80 wt.%, preferably from 0.1 wt.% to 30 wt.%, more preferably from 1 wt.% to 20 wt.%, and especially from 5 wt.% to 15 wt.%, based on the total weight of the composition.

[0540] In particular, the composition comprises a compound of formula (I) in an amount of from 0.001 wt.% to 20 wt.%, preferably from 0.005 wt.% to 6 wt.%, more preferably from 0.05 wt.% to 4 wt.%, and especially from 0.1 wt.% to 3 wt.%, based on the total weight of the composition.

[0541] The terms compound (I) and compound having the formula (I) are used interchangeably throughout the specification. Additionally, the terms compound (I) and compound having the formula (I) are used interchangeably throughout the specification.

[0542] Examples

[0543] The following provides a list of examples to further illustrate the disclosure and is not intended to limit the disclosure to the specific examples listed below.

[0544] 1. Use of at least one compound of formula (I)

[0545]

[0546] or a stereoisomer thereof as a fragrance chemical,

[0547] wherein,

[0548] R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0549] R2 is H or a straight-chain or branched C1-C4-alkyl,

[0550] or

[0551] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0552] R3 is H, a straight-chain or branched C1-C4-alkyl group, a straight-chain C1-C4-alkyl group substituted by C1-C2-alkylthio, or a phenyl group,

[0553] R4 is H or a straight-chain C1-C3 alkyl group, and

[0554] n is 0 or 1,

[0555] wherein the compound of formula (I) is not a compound wherein

[0556] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0557] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0558] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0559] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0560] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0561] 2. The use according to Example 1, which is to impart an aromatic effect to a composition; wherein the compound of formula (I) is not a compound wherein

[0562] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0563] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0564] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0565] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0566] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0567] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0568] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0569] 3. The use according to Example 1 or 2, wherein the compound of formula (I) is a compound of formula (Ia)

[0570]

[0571] wherein

[0572] R1 is selected from straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl, or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0573] R2 is selected from H, straight-chain or branched C1-C4-alkyl,

[0574] or

[0575] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0576] R3 is selected from H, straight-chain or branched C1-C4-alkyl, straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl,

[0577] R4 is H or methyl.

[0578] 4. The use according to Example 3, wherein,

[0579] R1 is straight-chain or branched C1-C8-alkyl or furyl (especially 2-furyl),

[0580] R2 is H or straight-chain or branched C1-C4-alkyl (especially H or straight-chain C1-C4-alkyl),

[0581] or

[0582] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered cycloalkyl ring (i.e., R1 and R2 together form a bridging group -(CH2)4- or -(CH2)5-),

[0583] R3 is H, methyl or phenyl, and

[0584] R4 is H or methyl.

[0585] 5. The use according to Example 4, wherein the compound having the formula (Ia) is selected from the following compounds:

[0586] Compound (Ia), wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0587] Compound (Ia), wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0588] Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0589] Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is phenyl and R4 is H;

[0590] Compound (Ia), wherein R1 is n-butyl, R2 is n-butyl, R3 is methyl and R4 is H;

[0591] Compound (Ia), wherein R1 is isopropyl, R2 is H, R3 is methyl and R4 is H;

[0592] Compound (Ia), wherein R1 is isobutyl, R2 is H, R3 is methyl and R4 is H;

[0593] Compound (Ia), wherein R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H;

[0594] Compound (Ia), wherein R1 is n-hexyl, R2 is H, R3 is H and R4 is H;

[0595] Compound (Ia), wherein R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H;

[0596] Compound (Ia), wherein R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H;

[0597] Compound (Ia), wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0598] Compound (Ia), wherein R1 is furan-2-yl, R2 is H, R3 is methyl and R4 is H;

[0599] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0600] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is methyl;

[0601] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is phenyl and R4 is H;

[0602] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and

[0603] Its mixture.

[0604] 6. Use according to embodiment 5, wherein the compound having formula (Ia) is selected from the following compounds:

[0605] Compound (Ia), wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0606] Compound (Ia), wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0607] Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0608] Compound (Ia), wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H;

[0609] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0610] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and

[0611] A mixture thereof.

[0612] 7. Use according to embodiment 6, wherein the compound having formula (Ia) is selected from the following compounds:

[0613] Compound (Ia), wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H;

[0614] Compound (Ia), wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0615] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H;

[0616] Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and

[0617] A mixture thereof.

[0618] 8. Use according to embodiment 7, wherein the compound having formula (Ia) is preferably a compound having formula (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H.

[0619] 9. Use according to embodiment 1, wherein the compound having formula (I) is a compound having formula (Ib)

[0620]

[0621] wherein

[0622] R1 is selected from linear or branched C1-C 11 -alkyl, linear or branched C2-C 11 -alkenyl, or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0623] R2 is selected from H, linear or branched C1-C4-alkyl,

[0624] or

[0625] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring,

[0626] R3 is selected from H, or linear C1-C3 alkyl, and

[0627] R4 is selected from H, or linear C1-C3 alkyl;

[0628] wherein preferably

[0629] R1 is linear C1-C6 alkyl,

[0630] R2 is H, or C1-C3 alkyl,

[0631] or R1 and R2 combine to form an unsubstituted 5-membered alicyclic ring,

[0632] R3 is selected from H, or linear C1-C3 alkyl, and

[0633] R4 is selected from H, or linear C1-C3 alkyl.

[0634] 10. The use according to any one of the foregoing embodiments, which use is as a fragrance.

[0635] 11. A method of imparting an aromatic effect to a composition, which comprises at least the following steps: adding at least one compound having formula (I) according to any one of embodiments 1 to 9 to the composition to be aromatized, or mixing at least one compound having formula (I) according to any one of embodiments 1 to 9 with other components of the composition simultaneously or continuously, or mixing at least one compound having formula (I) according to any one of embodiments 1 to 9 with a pre-formed mixture of a part of the other components of the composition;

[0636] wherein the compound having formula (I) is not a compound wherein

[0637] -n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0638] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0639] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0640] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0641] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0642] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0643] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0644] 12. The use or method according to any one of embodiments 1 to 11, 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.

[0645] 13. The use or method according to any one of embodiments 1 to 12, wherein the aromatic effect is selected from camphoraceous notes, nutty notes, technical notes, herbaceous notes, tobacco notes, balsamic notes, food notes, animal notes, aromatic notes, fresh notes, herbaceous notes, woody notes, green notes, floral notes, fruity notes, yeast notes, anise notes, notes reminiscent of isovaleraldehyde, wax notes, powdery notes, wine notes, mint notes, musty notes, aquatic notes, or a combination of two or more notes.

[0646] 14. The use or method according to any one of embodiments 1 to 13, wherein the compound having formula (I) is present in a total amount in the range of ≥0.01 wt.-% to ≤70.0 wt.-% based on the total weight of the composition.

[0647] 15. A composition comprising at least one compound having formula (I) according to any one of embodiments 1 to 3 and

[0648] a. at least one aroma chemical (X) different from the compound having formula (I), or

[0649] b. at least one non-aromatic chemical carrier, or

[0650] c. both (i) and (ii),

[0651] wherein the compound of formula (I) is not a compound wherein

[0652] - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0653] - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0654] - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0655] - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0656] - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0657] - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and

[0658] - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

[0659] 16. The composition according to embodiment 15, wherein the compound of formula (I) is present in a total amount in the range of ≥ 0.01 wt.-% to ≤ 70.0 wt.-% based on the total weight of the composition.

[0660] 17. A composition according to any one of embodiments 15 or 16, comprising at least one compound having formula (I), at least one aroma chemical (X) different from the compound having formula (I), and optionally at least one non-aromatic chemical carrier, wherein the at least one aroma chemical (X) different from the compound having 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, 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-heptenal, 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 the 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-n-methylionone, β-isomethylionone, α-irone, α-damascone, β-damascone, β-damascenone, δ-damascone, acetylated cedarwood oil, and mixtures thereof.

[0661] 18. The composition according to any one of embodiments 15 to 17, wherein the at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant active agents, or solvents.

[0662] 19. The composition according to embodiment 18, wherein the 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 solvents.

[0663] 20. A compound having the formula (I)

[0664]

[0665] or a stereoisomer thereof,

[0666] wherein

[0667] R1 is a straight-chain or branched C6-C 11 -alkyl, a straight-chain or branched C6-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0668] R2 is H or a straight-chain or branched C1-C4 alkyl,

[0669] or

[0670] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring,

[0671] R3 is H, a straight-chain or branched C1-C4-alkyl, a straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl,

[0672] R4 is H or a straight-chain C1-C3-alkyl,

[0673] n is 0 or 1;

[0674] wherein the compound of formula (I) is not a compound wherein

[0675] - n is 0, R1 is n - nonyl, R2 is H, R3 is methyl and R4 is H;

[0676] - n is 0, R1 is 4 - methylpent - 3 - enyl, R2 is methyl, R3 is methyl and R4 is H;

[0677] - n is 0, R1 is 1 - ethylpentyl (hept - 3 - yl), R2 is H, R3 is H and R4 is H;

[0678] - n is 0, R1 is 1 - propyl - hex - 1 - enyl (non - 4 - en - 4 - yl), R2 is H, R3 is H and R4 is H;

[0679] - n is 0, R1 is n - hexyl, R2 is methyl, R3 is methyl and R4 is H;

[0680] - n is 0, R1 and R2 together form -(CH2)4 -, R3 is methyl and R4 is methyl;

[0681] - n is 1, R1 is n - heptyl, R2 is H, R3 is methyl and R4 is H;

[0682] - n is 1, R1 is n - octyl, R2 is H, R3 is methyl and R4 is H;

[0683] - n is 1, R1 is n - hexyl, R2 is H, R3 is methyl and R4 is H; and

[0684] n is 1, R1 and R2 together form -(CH2)4 -, R3 is H and R4 is H.

[0685] 21. A compound of formula (Ia),

[0686]

[0687] wherein

[0688] R1 is a straight - chain or branched C1 - C 11 - alkyl, straight - chain or branched C2 - C 11 - alkenyl, or a 5 - membered unsaturated heterocycle containing an oxygen atom as a heteroatom,

[0689] R2 is H or a straight - chain or branched C1 - C4 alkyl,

[0690] or

[0691] R1 and R2 together with the carbon atom to which they are attached combine to form an unsubstituted 5 - membered alicyclic ring,

[0692] R3 is H, a straight-chain or branched C1-C4-alkyl group, a straight-chain C1-C4-alkyl group substituted with C1-C2-alkylthio, or phenyl, and R4 is H or methyl,

[0693] wherein the compound having the formula (Ia) is not a compound wherein

[0694] - R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H;

[0695] - R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H;

[0696] - R1 is isopropyl, R2 is H, R3 is H and R4 is H;

[0697] - R1 is n-propyl, R2 is H, R3 is methyl and R4 is H;

[0698] - R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H;

[0699] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0700] - R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl;

[0701] - R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H;

[0702] - R1 is 1-propyl-hex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H;

[0703] - R1 is methyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0704] - R1 is ethyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H;

[0705] - R1 is tert-butyl, R2 is H, R3 is 2-(methylthio)-ethyl and R4 is H;

[0706] - R1 is isopropyl, R2 is H, R3 is methyl and R4 is H;

[0707] - R1 is ethyl, R2 is methyl, R3 is methyl and R4 is H;

[0708] - R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H;

[0709] - R1 is tert-butyl, R2 is H, R3 is phenyl and R4 is H;

[0710] - R1 is isobutyl, R2 is H, R3 is methyl and R4 is H;

[0711] - R1 is tert - butyl, R2 is H, R3 is methyl and R4 is H;

[0712] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0713] - R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H;

[0714] - R1 is methyl, R2 is methyl, R3 is isopropyl and R4 is H;

[0715] - R1 is methyl, R2 is methyl, R3 is isobutyl and R4 is H;

[0716] - R1 is methyl, R2 is methyl, R3 is phenyl and R4 is H;

[0717] - R1 is tert - butyl, R2 is H, R3 is isopropyl and R4 is H;

[0718] - R1 is n - pentyl, R2 is H, R3 is methyl and R4 is H;

[0719] - R1 is n - hexyl, R2 is methyl, R3 is methyl and R4 is H; and

[0720] - R1 and R2 together form -(CH2)4 -, R3 is methyl and R4 is methyl.

[0721] 22. The compound according to Example 21, which is selected from the following compounds:

[0722] - Compound (Ia), wherein R1 is n - butyl, R2 is n - butyl, R3 is methyl and R4 is H;

[0723] - Compound (Ia), wherein R1 is n - hexyl, R2 is H, R3 is H and R4 is H;

[0724] - Compound (Ia), wherein R1 is n - hexyl, R2 is H, R3 is methyl and R4 is H;

[0725] - Compound (Ia), wherein R1 is n - octyl, R2 is H, R3 is methyl and R4 is H;

[0726] - Compound (Ia), wherein R1 is furan - 2 - yl, R2 is H, R3 is methyl and R4 is H; and

[0727] Its mixture.

[0728] 23. The compound according to embodiment 22, which is compound (Ia), wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H.

[0729] 24. A compound having the formula (Ib),

[0730]

[0731] wherein

[0732] R1 is a straight-chain C1-C6 alkyl group,

[0733] R2 is H, or a straight-chain C1-C3 alkyl group,

[0734] or

[0735] R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring,

[0736] R3 is H, or a straight-chain C1-C3 alkyl group,

[0737] R4 is H, or a straight-chain C1-C3 alkyl group;

[0738] wherein the compound having the formula (Ib) is not a compound wherein

[0739] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0740] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H;

[0741] - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl;

[0742] - R1 is methyl, R2 is H, R3 is methyl and R4 is H;

[0743] - R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; and

[0744] R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

[0745] Examples

[0746] 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.

[0747] 1. Analytical methods:

[0748] General GC method: 30m ZB-5 column, 0.25mm, 1.00um; Temperature program: 40 - 5 - 10 / 280 - 41

[0749] Inlet / Sampling / Detection: 0.2ul; 250℃; 300℃, 100; 1.11 c.p.; N2

[0750] NMR: Characterized by 1H-NMR and 13C-NMR. NMR spectra were measured on a Bruker DPX-500 spectrometer.

[0751] 2. Synthesis

[0752] General procedure for reacting hydroxycarboxylic acids with carbonyl compounds.

[0753] Add hydroxycarboxylic acid, carbonyl compound, and an acidic catalyst (amberlyst 15 or p-toluenesulfonic acid or sulfamic acid or sulfuric acid) to toluene in a reaction vessel equipped with a Dean-Stark apparatus and heat to reflux. Monitor the reaction by observing the formation of reaction water and via GC. Once the reaction is complete, cool the mixture to room temperature and quench with an aqueous NaHCO3 solution. Separate the phases, extract the aqueous phase several times with ethyl acetate or tert-butyl methyl ether. Wash the combined organic phases with saturated NaCl solution and water, dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the crude product by column chromatography or by distillation.

[0754] Example 1: Preparation of 2,2,5-trimethyl-1,3-dioxolan-4-one

[0755]

[0756] React lactic acid (90%, 15.0 g, 0.150 mol, 1.00 equivalent) with acetone (119 g, 2.04 mol, 13.6 equivalents) and Amberlyst 15 (100 mg) for 12 hours. Continuously collect the distillate while adding the same amount of fresh acetone to the reaction vessel. Filter the reaction mixture and carefully concentrate it in vacuo. Purify the crude product by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 80:20 to 0:100) to give the title compound (0.26 g) as a mixture of isomers with a purity of 98.4 GC-a% as a colorless liquid.

[0757] 1 1H NMR (500 MHz, DMSO) δ 4.67 (q, J = 6.8 Hz, 1H), 1.55 (s, 3H), 1.51 (s, 3H), 1.34 (d, J = 6.8 Hz, 3H).

[0758] 1313C NMR (126 MHz, DMSO) δ 173.73, 110.01, 69.73, 26.99, 25.11, 16.87.

[0759] Example 2: Preparation of 2,2 - diethyl - 5 - methyl - 1,3 - dioxolan - 4 - one

[0760]

[0761] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equivalent) was reacted with 3 - pentanone (12.9 g, 0.150 mol, 1.50 equivalents) and Amberlyst 15 (100 mg) in toluene (50 mL) for 7 hours. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 50:50) to yield the title compound (3.98 g) as an isomer mixture with a purity of 98.1 GC - a% as a colorless liquid.

[0762] 1H NMR (500 MHz, DMSO) δ 4.65 (q, J = 6.8 Hz, 1H), 1.87 - 1.69 (m, 5H), 1.35 (d, J = 6.9 Hz, 3H), 0.95 - 0.82 (m, 6H).

[0763] 13C NMR (126 MHz, DMSO) δ 173.69, 113.27, 70.07, 29.94, 29.20, 17.01, 7.44, 6.55.

[0764] Example 3: Preparation of 3 - methyl - 1,4 - dioxaspiro[4.4]nonan - 2 - one

[0765]

[0766] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 30.0 g, 0.300 mol, 1.00 equivalent) was reacted with cyclopentanone (37.9 g, 0.450 mol, 1.50 equivalents) and Amberlyst 15 (300 mg) in toluene (150 mL) for 29 hours. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 50 °C, 2.6 mbar) to yield the title compound (13.0 g) as an isomer mixture with a purity of 98.2 GC - a% as a colorless liquid.

[0767] 1¹H NMR (500 MHz, DMSO) δ 4.62 (q, J = 6.8 Hz, 1H), 2.08 - 1.84 (m, 4H), 1.76 - 1.62 (m, 4H), 1.34 (d, J = 6.8 Hz, 3H).

[0768] 13 ¹³C NMR (126 MHz, DMSO) δ 173.58, 119.41, 70.06, 36.35, 35.69, 22.87, 22.24, 16.42.

[0769] Example 4: Preparation of 3-methyl-1,4-dioxaspiro[4.5]decan-2-one

[0770]

[0771] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equivalent) was reacted with cyclohexanone (14.7 g, 0.150 mol, 1.50 equivalents) and p-toluenesulfonic acid (0.951 g, 5.00 mmol, 0.05 equivalent) in toluene (50 mL) for 23 hours. The reaction was quenched, extracted, and washed. The crude product was purified by Kugelrohr distillation at 126 °C - 157 °C and 2.5 mbar and SiO₂ column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 80:20 to 50:50 to 0:100) to yield the title compound (3.15 g) as a mixture of isomers with a purity of 97.5 GC-a% as a colorless liquid.

[0772] 1 ¹H NMR (500 MHz, DMSO) δ 4.66 (q, J = 6.8 Hz, 1H), 1.87 - 1.68 (m, 4H), 1.66 - 1.46 (m, 4H), 1.45 - 1.37 (m, 2H), 1.34 (d, J = 6.8 Hz, 3H).

[0773] 13 ¹³C NMR (126 MHz, DMSO) δ 173.60, 110.40, 69.34, 36.24, 34.28, 23.94, 22.81, 22.75, 17.12.

[0774] Example 5: Preparation of 2,2-dibutyl-5-methyl-1,3-dioxolan-4-one

[0775]

[0776] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equiv) was reacted with nonan-5-one (14.2 g, 0.100 mol, 1.00 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 50 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to afford the title compound (2.81 g) as a mixture of isomers in the form of a colorless liquid with a purity of 97.9 GC-a%.

[0777] 1 1H NMR (500 MHz, DMSO) δ 4.65 (q, J = 6.8 Hz, 1H), 1.84 - 1.67 (m, 4H), 1.38 - 1.22 (m, 11H), 0.92 - 0.82 (m, 6H).

[0778] 13 13C NMR (126 MHz, DMSO) δ 173.73, 112.87, 69.90, 36.81, 36.36, 25.07, 24.28, 22.11, 21.98, 17.05, 13.81, 13.79.

[0779] Example 6: Preparation of 2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one

[0780]

[0781] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equiv) was reacted with 3,3-dimethylbutan-2-one (10.0 g, 0.100 mol, 1.00 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 12 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to afford the title compound (1.00 g) as a mixture of isomers in the form of a colorless liquid with a purity of 99.1 GC-a%.

[0782] 1 1H NMR (500 MHz, DMSO) δ 4.75 - 4.60 (m, 1H), 1.49 - 1.45 (m, 3H), 1.40 - 1.30 (m, 3H), 0.98 - 0.91 (m, 9H).

[0783] 1313C NMR (126 MHz, DMSO) δ 173.82, 173.66, 115.60, 114.50, 71.44, 69.51, 37.49, 24.17, 24.13, 22.84, 18.97, 18.95, 16.10.

[0784] Example 7: Preparation of 2-Isopropyl-5-methyl-1,3-dioxolan-4-one

[0785]

[0786] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equivalent) was reacted with 2-methylpropanal (7.21 g, 0.100 mol, 1.00 equivalent) and Amberlyst 15 (100 mg) in toluene (50 mL) for 13 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to afford the title compound (3.06 g) as a mixture of isomers in the form of a colorless liquid with a purity of 99.9 GC-a%.

[0787] 1 1H NMR (500 MHz, DMSO) δ 5.58 - 5.36 (m, 1H), 4.65 - 4.50 (m, 1H), 1.97 - 1.84 (m, 1H), 1.38 - 1.28 (m, 3H), 0.98 - 0.78 (m, 6H).

[0788] 13 13C NMR (126 MHz, DMSO) δ 174.03, 173.98, 107.20, 106.44, 70.80, 69.88, 31.90, 31.06, 15.95, 15.77, 15.74, 15.73, 15.55.

[0789] Example 8: Preparation of 2-Isobutyl-5-methyl-1,3-dioxolan-4-one

[0790]

[0791] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equiv) was reacted with 3-methylbutanal (8.61 g, 0.100 mol, 1.00 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 7 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 80:20 to 0:100) to give the title compound (4.47 g) as an isomeric mixture in the form of a colorless liquid with a purity of 99.8 GC-a%.

[0792] 1 1H NMR (500 MHz, DMSO) δ 5.88 - 5.59 (m, 1H), 4.64 - 4.45 (m, 1H), 1.87 - 1.57 (m, 3H), 1.39 - 1.29 (m, 3H), 0.97 - 0.89 (m, 6H).

[0793] 13 13C NMR (126 MHz, DMSO) δ 174.07, 173.96, 103.40, 102.88, 70.81, 69.29, 42.29, 41.99, 23.51, 23.42, 22.60, 22.52, 22.50, 15.93, 15.36.

[0794] Example 9: Preparation of 2-Hexyl-5-methyl-1,3-dioxolan-4-one

[0795]

[0796] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equiv) was reacted with heptanal (12.0 g, 0.100 mol, 1.00 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 28 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 80:20 to 0:100) to give the title compound (3.32 g) as an isomeric mixture in the form of a pale yellow liquid with a purity of 99.9 GC-a%.

[0797] 11H NMR (500 MHz, DMSO) δ 5.82 - 5.50 (m, 1H), 4.69 - 4.43 (m, 1H), 1.80 - 1.67 (m, 2H), 1.47 - 1.18 (m, 11H), 0.96 - 0.79 (m, 3H).

[0798] 13 13C NMR (126 MHz, DMSO) δ 174.03, 173.92, 104.12, 103.50, 70.83, 69.43, 33.68, 33.13, 31.13, 31.11, 28.32, 28.29, 22.57, 22.28, 21.99, 15.93, 15.46, 13.90.

[0799] Example 10: Preparation of 5-Methyl-2-octyl-1,3-dioxolan-4-one

[0800]

[0801] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 10.0 g, 0.100 mol, 1.00 equivalent) was reacted with nonanal (14.2 g, 0.100 mol, 1.00 equivalent) and Amberlyst 15 (100 mg) in toluene (50 mL) for 22 hours. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to give the title compound (2.32 g) as a mixture of isomers with a purity of 99.0 GC-a% as a colorless liquid.

[0802] 1 1H NMR (500 MHz, DMSO) δ 5.79 - 5.50 (m, 1H), 4.65 - 4.44 (m, 1H), 1.77 - 1.68 (m, 2H), 1.42 - 1.17 (m, 15H), 0.89 - 0.81 (m, 3H).

[0803] 13 13C NMR (126 MHz, DMSO) δ 174.07, 173.96, 104.14, 103.52, 70.85, 69.44, 33.68, 33.12, 31.30, 31.29, 28.90, 28.87, 28.68, 28.65, 28.63, 22.64, 22.34, 22.14, 15.95, 15.48, 13.98.

[0804] Example 11: Preparation of 2-(Furan-2-yl)-5-methyl-1,3-dioxolan-4-one

[0805]

[0806] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 50.0 g, 0.500 mol, 1.00 equivalent) was reacted with furfural (48.0 g, 0.500 mol, 1.00 equivalent) and Amberlyst 15 (500 mg) in toluene (250 mL) for 22 h. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 60 °C - 84 °C, 1.8 mbar - 3.2 mbar) to yield the title compound (18.9 g) as a mixture of isomers in the form of a colorless liquid with a purity of 99.3 GC-a%.

[0807] 1 H NMR (500 MHz, DMSO) δ 7.86 - 7.76 (m, 1H), 6.89 - 6.81 (m, 1H), 6.79 - 6.59 (m, 1H), 6.57 - 6.52 (m, 1H), 4.92 - 4.58 (m, 1H), 1.51 - 1.35 (m, 3H).

[0808] 13 C NMR (126 MHz, DMSO) δ 173.45, 173.42, 148.26, 147.04, 145.23, 144.96, 112.59, 111.35, 110.86, 110.78, 95.99, 95.83, 71.07, 69.56, 59.82, 20.79, 16.25, 15.89, 14.10.

[0809] Example 12: Preparation of 2,2 - diethyl - 5 - phenyl - 1,3 - dioxolan - 4 - one

[0810]

[0811] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, hydroxy(phenyl)acetic acid (15.2 g, 0.100 mol, 1.00 equivalent) was reacted with 3 - pentanone (12.9 g, 0.150 mol, 1.50 equivalents) and Amberlyst 15 (100 mg) in toluene (50 mL) for 8 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 80:20 to 0:100) to yield the title compound (2.07 g) as a mixture of isomers in the form of a colorless liquid with a purity of 99.9 GC-a%.

[0812] 1 1H NMR (500 MHz, DMSO) δ 7.49 - 7.36 (m, 5H), 5.74 (s, 1H), 1.93 (q, J = 7.5 Hz, 4H), 0.96 (t, J = 7.5 Hz, 6H).

[0813] 13 13C NMR (126 MHz, DMSO) δ 171.69, 134.98, 128.88, 128.70, 126.95, 113.95, 75.39, 29.49, 29.23, 7.76, 7.19.

[0814] Example 13: Preparation of 3 - phenyl - 1,4 - dioxaspiro[4.4]nonan - 2 - one

[0815]

[0816] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, hydroxy(phenyl)acetic acid (15.2 g, 0.100 mol, 1.00 equivalent) was reacted with cyclopentanone (12.6 g, 0.150 mol, 1.50 equivalents) and Amberlyst 15 (100 mg) in toluene (50 mL) for 140 hours. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to give the title compound (4.51 g) as a mixture of isomers with a purity of 98.7 GC - a% as a pale yellow solid.

[0817] 1 1H NMR (500 MHz, DMSO) δ 7.49 - 7.33 (m, 5H), 5.69 (s, 1H), 2.20 - 1.94 (m, 4H), 1.80 - 1.68 (m, 4H).

[0818] 13 13C NMR (126 MHz, DMSO) δ 171.57, 134.76, 129.04, 128.75, 127.09, 120.11, 75.63, 36.28, 36.13, 22.97, 22.28.

[0819] Example 14: Preparation of 2 - isobutyl - 5 - phenyl - 1,3 - dioxolan - 4 - one

[0820]

[0821] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, hydroxy(phenyl)acetic acid (15.2 g, 0.100 mol, 1.00 equiv) was reacted with 3-methylbutanal (8.61 g, 0.100 mol, 1.00 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 35 h. The reaction was quenched, extracted, and washed. The crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 80:20 to 0:100) to afford the title compound (3.90 g) as a mixture of isomers in 97.3 GC-a% purity as a colorless solid.

[0822] 1 1H NMR (500 MHz, DMSO) δ 7.55 - 7.34 (m, 5H), 5.93 - 5.74 (m, 1H), 5.54 - 5.46 (m, 1H), 1.93 - 1.73 (m, 3H), 1.02 - 0.92 (m, 6H).

[0823] 13 13C NMR (126 MHz, DMSO) δ 172.04, 134.42, 129.08, 128.69, 127.35, 103.33, 76.32, 42.05, 23.49, 22.62.

[0824] Example 15: 2-Hexyl-2,5-dimethyl-1,3-dioxolan-4-one

[0825]

[0826] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, lactic acid (90%, 20.0 g, 0.200 mol, 1.00 equiv) was reacted with 2-octanone (12.8 g, 0.100 mol, 0.50 equiv) and Amberlyst 15 (100 mg) in toluene (50 mL) for 28 h. The reaction was quenched, extracted, and washed. The crude product was concentrated at 70 °C - 120 °C and 3.2 mbar and purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 80:20 to 0:100) to afford the title compound (3.18 g) as a mixture of isomers in 98.3 GC-a% purity as a colorless liquid.

[0827] 1 1H NMR (500 MHz, DMSO) δ 4.72 - 4.59 (m, 1H), 1.85 - 1.67 (m, 2H), 1.49 (d, J = 11.7 Hz, 3H), 1.41 - 1.19 (m, 11H), 0.90 - 0.79 (m, 3H).

[0828] 13 C NMR (126 MHz, DMSO) δ 173.72, 173.68, 111.73, 111.22, 70.01, 69.46, 38.77, 38.27, 31.11, 31.09, 28.55, 28.45, 25.20, 23.74, 23.18, 22.30, 21.99, 17.43, 16.54, 13.91, 13.90。

[0829] Example 16: 2-Hexyl-1,3-dioxolan-4-one

[0830]

[0831] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, glycolic acid (25.0 g, 0.325 mol, 1.00 equivalent) was reacted with heptanal (18.6 g, 0.163 mol, 0.50 equivalent) and sulfamic acid (316 mg, 3.25 mmol, 0.02 equivalent) in toluene (70 mL) for 5 hours. The reaction was quenched, extracted, and washed. 4 g of the crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 95:5 to 90:10 to 0:100) to give the title compound (2.00 g) as a mixture of isomers with a purity of 96.3 GC-a% as a colorless liquid.

[0832] 1 H NMR (500 MHz, DMSO) δ 5.67 (t, J = 5.0 Hz, 1H), 4.47 - 4.26 (m, 2H), 1.74 (dt, J = 8.7, 5.6 Hz, 2H), 1.42 - 1.17 (m, 10H), 0.86 (t, J = 6.9 Hz, 3H).

[0833] 13 C NMR (126 MHz, DMSO) δ 172.04, 105.99, 63.67, 33.29, 31.12, 28.32, 22.38, 21.99, 13.87。

[0834] Example 17: 3,3-Dimethyl-1,4-dioxaspiro[4.4]nonan-2-one

[0835]

[0836] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, 2-hydroxyisobutyric acid (10.0 g, 0.0961 mol, 1.00 equiv) was reacted with cyclopentanone (4.04 g, 0.0480 mol, 0.50 equiv) and sulfamic acid (93 mg, 0.961 mmol, 0.02 equiv) in toluene (25 mL) for 5 h. Four drops of concentrated sulfuric acid were added and the mixture was stirred for an additional 6 h under reflux. The reaction was quenched, extracted, and washed. 4 g of the crude product was purified by SiO2 column chromatography (cyclohexane / ethyl acetate 100:0 to 90:10 to 0:100) to afford the title compound (0.28 g) as a colorless liquid with a purity of 97.9 GC-a%.

[0837] 1 1H NMR (500 MHz, DMSO) δ 2.03 - 1.81 (m, 4H), 1.78 - 1.62 (m, 4H), 1.39 (s, 6H).

[0838] 13 13C NMR (126 MHz, DMSO) δ 175.06, 118.56, 76.75, 37.70, 24.89, 22.49.

[0839] Example 18: Preparation of (5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one

[0840]

[0841] According to the general procedure for the reaction of hydroxycarboxylic acids with carbonyl compounds, L-lactic acid (80%, 169 g, 1.50 mol, 1.00 equiv) was reacted with 3,3-dimethylbutan-2-one (75.1 g, 0.750 mol, 0.50 equiv) and sulfamic acid (1.46 g, 15.0 mmol, 0.02 equiv) in toluene (375 mL) for 6 h. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 49 °C - 45 °C, 3.7 mbar - 2.8 mbar) to afford the title compound (28.4 g) as a colorless liquid with a purity of 99.8 GC-a% as a mixture of isomers.

[0842] 1 1H NMR (500 MHz, DMSO) δ 4.78 - 4.57 (m, 1H), 1.49 (s, 3H), 1.41 - 1.28 (m, 3H), 0.98 - 0.90 (m, 9H).

[0843] 1313C NMR (126 MHz, DMSO) δ 173.77, 173.61, 115.55, 114.46, 71.40, 69.47, 39.42, 37.46, 22.81, 18.94, 18.92, 16.07.

[0844] [α] D 20 : +30.2° (c 0.95, CHCl3)

[0845] Example 19: Preparation of (5R)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one

[0846]

[0847] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, D-lactic acid (90%, 150 g, 1.50 mol, 1.00 equivalent) was reacted with 3,3-dimethylbutan-2-one (75.1 g, 0.750 mol, 0.50 equivalent) and sulfamic acid (1.46 g, 15.0 mmol, 0.02 equivalent) in toluene (375 mL) for 6 hours. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 48 °C - 31 °C, 3.4 mbar - 2.8 mbar) to give the title compound (41.8 g) as a mixture of isomers with a purity of 99.8 GC-a% as a colorless liquid.

[0848] 1 1H NMR (500 MHz, DMSO) δ 4.76 - 4.58 (m, 1H), 1.53 - 1.44 (m, 3H), 1.42 - 1.30 (m, 3H), 1.04 - 0.85 (m, 9H).

[0849] 13 13C NMR (126 MHz, DMSO) δ 173.77, 173.61, 115.56, 114.46, 71.40, 69.48, 39.42, 37.46, 24.15, 24.11, 22.81, 18.94, 18.93, 16.07.

[0850] [α] D 20 : -30.2° (c 0.94, CHCl3)

[0851] Example 20: Preparation of (3S)-3-methyl-1,4-dioxaspiro[4.4]nonan-2-one

[0852]

[0853] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, L-lactic acid (80%, 56.3 g, 0.500 mol, 1.00 equivalent) was reacted with cyclopentanone (63.1 g, 0.750 mol, 1.50 equivalents) and Amberlyst 15 (500 mg) in toluene (250 mL) for 51 h. Additional Amberlyst 15 (500 mg) was added and the mixture was reacted for an additional 25 h. Additional L-lactic acid (56.3 g) was added and the mixture was reacted for an additional 27 h. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 59 °C - 61 °C, 2.8 mbar) to give the title compound (23.5 g) as a colorless liquid with a purity of 96.4 GC-a%.

[0854] 1 1H NMR (500 MHz, DMSO) δ 4.62 (q, J = 6.8 Hz, 1H), 2.07 - 1.83 (m, 4H), 1.75 - 1.61 (m, 4H), 1.34 (d, J = 6.8 Hz, 3H).

[0855] 13 13C NMR (126 MHz, DMSO) δ 173.59, 119.42, 70.05, 36.34, 35.68, 22.84, 22.23, 16.43.

[0856] [α] D 20 : +24.9° (c 0.94, CHCl3)

[0857] Example 21: Preparation of (3R)-3-methyl-1,4-dioxaspiro[4.4]nonan-2-one

[0858]

[0859] According to the general procedure for reacting hydroxycarboxylic acids with carbonyl compounds, D-lactic acid (90%, 50.0 g, 0.500 mol, 1.00 equivalent) was reacted with cyclopentanone (21.0 g, 0.250 mol, 0.50 equivalent) and sulfamic acid (485 mg, 5.00 mmol, 0.02 equivalent) in toluene (125 mL) for 5 h. The reaction was quenched, extracted, and washed. The crude product was purified by distillation (T 头 = 46 °C - 62 °C, 3 mbar - 4 mbar) to give the title compound (7.94 g) as a colorless liquid with a purity > 99.9 GC-a%.

[0860] 11H NMR (500 MHz, DMSO) δ 4.62 (q, J = 6.8 Hz, 1H), 2.08 - 1.83 (m, 4H), 1.75 - 1.60 (m, 4H), 1.34 (d, J = 6.8 Hz, 3H).

[0861] 13 13C NMR (126 MHz, DMSO) δ 173.61, 119.43, 70.05, 36.34, 35.68, 22.84, 22.22, 16.44.

[0862] [α] D 20 : -26.9° (c 0.89, CHCl3)

[0863] 3. Olfactory evaluation

[0864] In order to test the quality and intensity of the compounds and mixtures of the present invention, aroma strip tests were conducted.

[0865] For this purpose, absorption strips were soaked in a solution containing 1 wt.% to 10 wt.% of the compound to be tested in triethyl citrate. After the solvent had evaporated (about 30 s), the aroma effect was evaluated olfactorily by trained perfumers.

[0866] The aromatic effects of the compounds of the present invention are indicated in Table 1 below. The compounds of the present invention were labeled as Compound A and formulated in perfume compositions according to Tables 2 and 3.

[0867] Table 1: Compounds of the present invention

[0868]

[0869]

[0870]

[0871] 4. Advantageous compositions

[0872] The compounds indicated in Table 1 were each formulated as compositions according to Tables 2 and 3. The compounds from Table 1 were labeled "Compound A" in Tables 2 and 3.

[0873] Table 2: Compositions 1A and 1B

[0874]

[0875] Table 3: Compositions 2A and 2B

[0876]

[0877]

[0878] The compositions according to Tables 2 and 3, namely 1A, 1B, 2A, and 2B, can be included in various compositions selected from the group consisting of: deodorant pump sprays, cleansing conditioners, facial wash gels, foam bath concentrates, hairsprays, self-foaming body washes, sprayable sun care lotions, sprayable sun protection lotions, emollient facial wash 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 setting 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 creams, facial cleansers, body lotions, sunscreen SPF50+, sprayable emulsions, hand dishwashing detergents - regular, hand dishwashing detergents - concentrates, sanitary cleansers - concentrates, multi-purpose cleaners, antibacterial fabric softeners, detergent compositions, powder detergent compositions, and liquid detergent compositions.

[0879] Those skilled in the art may be proficient in various general formulations of the above products.

[0880] 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 [New Aroma Chemicals], pages 6 to 46, Tables 1 to D13, where "Fragrance Composition 1A" is replaced with an equal amount of Composition 1A, 1B, 2A, or 2B.

Claims

1. Use of at least one compound of formula (I) or its stereoisomers as an aroma chemical, wherein R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom, R2 is H or straight-chain or branched C1-C4-alkyl, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring, R3 is H, straight-chain or branched C1-C4-alkyl, straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl, R4 is H or straight-chain C1-C3 alkyl, and n is 0 or 1, wherein the compound of formula (I) is not a compound wherein - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H; - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

2. The use according to claim 1, which is to impart an aromatic effect to a composition; wherein the compound of formula (I) is not a compound wherein - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H; - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

3. The use according to any one of claims 1 or 2, wherein The compound of formula (I) is a compound of formula (Ia), wherein R1 is a straight-chain or branched C1-C 11 -alkyl group, a straight-chain or branched C2-C 11 -alkenyl group or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom, R2 is H or straight-chain or branched C1-C4-alkyl, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring, R3 is H, straight-chain or branched C1-C4 alkyl, straight-chain C1-C4-alkyl substituted with C1-C2-alkylthio, or phenyl, and R4 is H or methyl.

4. The use according to claim 3, wherein, R1 is straight-chain or branched C1-C8-alkyl or furyl, R2 is H or straight-chain or branched C1-C4 alkyl, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered cycloalkyl ring (i.e., R1 and R2 together form a bridging group -(CH2)4- or -(CH2)5-), R3 is H, methyl or phenyl, and R4 is H or methyl.

5. The use according to claim 4, wherein, The compound of formula (Ia) is selected from the following compounds: - Compound (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is phenyl and R4 is H; - Compound (Ia) wherein R1 is n-butyl, R2 is n-butyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is isopropyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is isobutyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H; - Compound (Ia) wherein R1 is n-hexyl, R2 is H, R3 is H and R4 is H; - Compound (Ia) wherein R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is furan-2-yl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is methyl; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is phenyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and - A mixture thereof.

6. The use according to claim 5, wherein, The compound of formula (Ia) is selected from the following compounds: - Compound (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is methyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and - A mixture thereof.

7. The use according to claim 6, wherein The compound of formula (Ia) is selected from the following compounds: - Compound (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H; - Compound (Ia) wherein R1 and R2 together form a bridging group -(CH2)4-, R3 is methyl and R4 is H; - Compound (Ia), wherein R1 and R2 together form a bridging group -(CH2)5-, R3 is methyl and R4 is H; and - A mixture thereof; wherein the compound of formula (Ia) is preferably a compound of formula (Ia) wherein R1 is tert-butyl, R2 is methyl, R3 is methyl and R4 is H.

8. Use according to any one of claims 1 or 2, wherein The compound of formula (I) is a compound of formula (Ib), wherein R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom, R2 is H or a straight-chain or branched C1-C4-alkyl group, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5- or 6-membered alicyclic ring, R3 is H or a straight-chain C1-C3-alkyl group, R4 is H or a straight-chain C1-C3-alkyl group; wherein preferably R1 is a straight-chain C1-C6-alkyl group, R2 is H or a straight-chain C1-C3-alkyl group, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring, R3 is H or a straight-chain C1-C3-alkyl group, R4 is H or a straight-chain C1-C3-alkyl group.

9. The use according to any one of the preceding claims, which use is as a fragrance.

10. A method of imparting an aromatic effect, preferably a fragrance, to a composition, which method comprises at least the following steps: adding at least one compound of formula (I) according to any one of claims 1 to 8 to the composition to be aromatized, or mixing at least one compound of formula (I) according to any one of claims 1 to 8 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 to 8 with a pre-formed mixture of a part of the other components of the composition; wherein the compound of formula (I) is not a compound wherein - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H; - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

11. The use or method according to any one of claims 1 to 10, 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.

12. The use or method according to any one of claims 1 to 11, wherein, The aromatic effect is selected from camphor notes, nutty notes, technical notes, herbaceous notes, tobacco notes, balsamic notes, food notes, animal notes, floral notes, fresh notes, herbaceous notes, woody notes, green leafy notes, floral fragrance notes, fruity notes, yeast notes, anise notes, notes reminiscent of isovaleraldehyde, wax notes, powdery notes, wine notes, or a combination of two or more notes.

13. The use or method according to any one of claims 1 to 12, 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.

14. A composition comprising at least one compound of formula (I) according to any one of claims 1 to 8 and a. at least one aroma chemical (X) different from the compound of formula (I), or b. at least one non-aromatic chemical carrier, or c. both (i) and (ii); wherein the compound of formula (I) is not a compound wherein - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-propyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H; - n is 0, R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; and - n is 0, R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl.

15. The composition according to claim 14, which comprises at least one compound of formula (I) according to any one of claims 1 to 8, at least one aroma chemical (X) different from the compound of formula (I), and optionally at least one non-aromatic chemical carrier, wherein the at least one aroma 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, 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 the 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.

16. The composition according to any one of claims 14 or 15, wherein The compound of formula (I) is present in a total amount in the range of ≥ 0.01 wt.-% to ≤ 70.0 wt.-% based on the total weight of the composition.

17. The composition according to any one of claims 14 to 16, wherein, The at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorant active agents, or solvents.

18. A compound of formula (I) or a stereoisomer thereof, wherein R1 is a straight-chain or branched C6-C 11 -alkyl group, a straight-chain or branched C6-C 11 -alkenyl group or a 5-membered unsaturated heterocyclic ring containing an oxygen atom as a heteroatom, R2 is H or a straight-chain or branched C1-C4 alkyl group, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring, R3 is H, a straight-chain or branched C1-C4-alkyl group, a straight-chain C1-C4-alkyl group substituted with a C1-C2-alkylthio group, or phenyl, R4 is H or a straight-chain C1-C3-alkyl group, n is 0 or 1; wherein the compound of formula (I) is not a compound wherein - n is 0, R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H; - n is 0, R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H; - n is 0, R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H; - n is 0, R1 is 1-propyl-hex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-hexyl, R2 is H, R3 is H and R4 is H; - n is 0, R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H; - n is 0, R1 and R2 together form -(CH2)4-, R3 is methyl and R4 is methyl; - n is 1, R1 is n-heptyl, R2 is H, R3 is methyl and R4 is H; - n is 1, R1 is n-octyl, R2 is H, R3 is methyl and R4 is H; - n is 1, R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; and -n is 1, R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

19. A compound having the formula (Ia), wherein R1 is a straight-chain or branched C1-C 11 -alkyl, straight-chain or branched C2-C 11 -alkenyl, or a 5-membered unsaturated heterocycle containing an oxygen atom as a heteroatom, R2 is H or a straight-chain or branched C1-C4 alkyl group, or R1 and R2, together with the carbon atom to which they are attached, combine to form an unsubstituted 5-membered cycloaliphatic ring, R3 is H, a straight-chain or branched C1-C4-alkyl group, a straight-chain C1-C4-alkyl group substituted with C1-C2-alkylthio, or phenyl, and R4 is H or methyl, wherein the compound having the formula (Ia) is not a compound wherein - R1 is n-nonyl, R2 is H, R3 is methyl and R4 is H; - R1 is 4-methylpent-3-enyl, R2 is methyl, R3 is methyl and R4 is H; - R1 is isopropyl, R2 is H, R3 is H and R4 is H; - R1 is n-propyl, R2 is H, R3 is methyl and R4 is H; - R1 is isopropyl, R2 is H, R3 is phenyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; - R1 is methyl, R2 is methyl, R3 is ethyl and R4 is ethyl; - R1 is 1-ethylpentyl (hept-3-yl), R2 is H, R3 is H and R4 is H; - R1 is 1-propyl-hex-1-enyl (non-4-en-4-yl), R2 is H, R3 is H and R4 is H; - R1 is methyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H; - R1 is ethyl, R2 is methyl, R3 is 2-(methylthio)-ethyl and R4 is H; - R1 is tert-butyl, R2 is H, R3 is 2-(methylthio)-ethyl and R4 is H; - R1 is isopropyl, R2 is H, R3 is methyl and R4 is H; - R1 is ethyl, R2 is methyl, R3 is methyl and R4 is H; - R1 is isobutyl, R2 is H, R3 is phenyl and R4 is H; - R1 is tert-butyl, R2 is H, R3 is phenyl and R4 is H; - R1 is isobutyl, R2 is H, R3 is methyl and R4 is H; - R1 is tert-butyl, R2 is H, R3 is methyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H; - R1 is ethyl, R2 is ethyl, R3 is methyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is isopropyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is isobutyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is phenyl and R4 is H; - R1 is tert-butyl, R2 is H, R3 is isopropyl and R4 is H; - R1 is n-pentyl, R2 is H, R3 is methyl and R4 is H; - R1 is n-hexyl, R2 is methyl, R3 is methyl and R4 is H; and - R1 and R2 together form -(CH2)4-, R3 is methyl and R4 is methyl.

20. The compound according to claim 19, which is selected from the following compounds: - Compound (Ia), wherein R1 is n-butyl, R2 is n-butyl, R3 is methyl and R4 is H; - Compound (Ia), wherein R1 is n-hexyl, R2 is H, R3 is H and R4 is H; - Compound (Ia), wherein R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia), wherein R1 is n-octyl, R2 is H, R3 is methyl and R4 is H; - Compound (Ia), wherein R1 is furan-2-yl, R2 is H, R3 is methyl and R4 is H; and - A mixture thereof.

21. The compound according to claim 20, which is compound (Ia), wherein, R1 is n-octyl, R2 is H, R3 is methyl and R4 is H.

22. A compound having the formula (Ib), wherein R1 is a straight-chain C1-C6 alkyl group, R2 is H, or a straight-chain C1-C3 alkyl group, or R1 and R2 together with the carbon atom to which they are bonded combine to form an unsubstituted 5-membered alicyclic ring, R3 is H, or a straight-chain C1-C3 alkyl group, R4 is H, or a straight-chain C1-C3 alkyl group; wherein the compound having the formula (Ib) is not a compound wherein - R1 is methyl, R2 is H, R3 is methyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is methyl and R4 is H; - R1 is methyl, R2 is methyl, R3 is methyl and R4 is methyl; - R1 is n-hexyl, R2 is H, R3 is methyl and R4 is H; and - R1 and R2 together form -(CH2)4-, R3 is H and R4 is H.

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