NEW FRAGRANCES WITH ROSE SCENT
Patent Information
- Authority / Receiving Office
- DE · DE
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2018-07-23
- Publication Date
- 2026-03-19
AI Technical Summary
The perfume and flavor industry lacks fragrance and flavoring substances that can create complex olfactory impressions by harmonizing with floral and fruity notes, and existing odor perception mechanisms and chemical structure relationships are not well understood, leading to unpredictable sensory changes.
The use of compounds of formula (I) and (II) with specific structural variations, such as 4-isopentylcyclohex-2-en-1-ol and 2-isopentylcyclohex-2-en-1-one, which exhibit unique olfactory properties, including rosy and fruity notes, and possess high stability and substantivity, enhancing and modifying floral and woody notes.
These compounds provide novel fragrance and flavor compositions with complex sensory profiles, offering high stability, adhesion, and odor-enhancing properties, enabling the creation of innovative perfumes and flavors with enhanced naturalness and freshness.
Description
[0001] The present invention primarily relates to the use of compounds of the following formula (I) as odorants and / or flavorings. The invention also relates to odorant and / or flavoring compositions containing one or more of these compounds, perfumed and flavored articles comprising one or more of these compounds, and corresponding methods for conveying, modifying, and / or enhancing certain odorant and / or flavor notes.
[0002] For example, US 2010 / 0130397 describes the use of 4-isoamylcyclohexanol as a flavoring agent. WO 2007 / 009982 A1 discloses the use of 4-isoamylcyclohexanone as a fragrance or flavoring agent with a rose-geranium note.
[0003] Despite the abundance of existing fragrance and flavoring substances, the perfume and flavor industry continues to experience a general demand for new ones. For example, there is a need for fragrance or flavoring substances that, in addition to a primary scent or flavor note, can create further interesting notes within fragrance or flavor compositions and expand the perfumer's creative possibilities with their novel or original olfactory properties. In particular, there is interest in fragrance and / or flavoring substances with scent notes that can harmonize with floral and / or fruity fragrance and / or flavoring substances. Ideally, the different olfactory aspects and notes should overlap to create an overall complex olfactory impression.
[0004] The creation of novel compositions requires a constant supply of fragrance and / or flavoring substances with distinctive sensory properties, suitable as the foundation for composing innovative perfumes with complex sensory characteristics. Preferred fragrance and / or flavoring substances should, in addition to a specific note, possess further notes and aspects that lend them character and complexity.
[0005] The search for suitable rose-like materials, which led to the present invention, was made more difficult by the following circumstances: i) the mechanisms of odor perception are not sufficiently understood; ii) the relationships between the specific odor perception on the one hand and the chemical structure of the associated odorant and / or flavoring agent on the other hand are not sufficiently researched; iii) often even minor changes to the structural composition of a known odorant and / or flavoring agent cause significant changes in its sensory properties and impair its tolerability for the human organism.
[0006] The success of the search for suitable odor and / or aroma substances therefore depends heavily on the intuition of the searcher.
[0007] The primary task was now to find fragrance and / or flavoring substances that have an interesting, preferably complex, and original sensory profile and are suitable as fragrance or flavoring substances for use in perfumery.
[0008] Within the scope of the present invention, substances were sought that could exhibit, impart, modify, and / or intensify one, several, or all of the following notes: green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, oily, metallic, and balsamic. In particular, substances with notes were sought that preferably exhibit at least one of the floral and / or fruity notes and preferably also have a rose-like scent or impart a rose note.
[0009] The substances sought should enable the production of novel fragrance and / or flavor compositions with distinctive olfactory notes and characteristics. Substances particularly suitable for combination with other fragrance and / or flavoring substances exhibiting woody, floral, and / or fruity notes would be advantageous.
[0010] In addition, the odorants and / or flavorings fulfilling this primary task should preferably possess additional positive secondary properties beyond their primary, namely odorous, properties, such as high stability under certain application conditions, high yield, good adhesion, high substantivity, odor-enhancing properties (so-called booster or enhancer effect) and / or round off the naturalness, freshness, richness, (radiance) power and / or radiance of other odorants and / or flavorings, so that sensorially remarkable effects can be achieved.
[0011] Another object of the invention relates to the production of such novel odor and / or flavoring substances in any form, their isomers, and their mixtures.
[0012] Another task involves the provision of new compounds for use as fragrances and flavorings, preferred mixtures, as well as consumer goods containing these mixtures and their manufacture.
[0013] These problems are solved by the combinations of features defined in the main claims. Preferred embodiments are the subject of the dependent claims. Summary of the invention
[0014] The invention relates in a first aspect to the use of a compound of formula (I), where X represents a -CHO, a -OH, or a -CH2OH group, where a single bond or a double bond is present at the respective location of one of the dashed lines, wherein if X is an OH group, at least one double bond is present, and wherein the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho-, meta-, or para-position to the X group, provided that if a double bond is present in the ring, then the 3-isopentyl or 3-isopent-2-enyl residue is directly bonded to this double bond as an ortho- or meta-substituent, as a fragrance and / or flavoring agent.
[0015] A particularly preferred alternative here and in the following is the use of a compound of formula (1a), where X represents a -CHO, a -OH, or a -CH2OH group, at the respective location of one of the dashed lines there is either a single bond or a double bond, where if X is an OH group there is at least one double bond, as a fragrance and / or flavoring agent.
[0016] Another particularly preferred alternative, here and in the following, is the use of a compound of formula (Ib), where X represents a -CHO, a -OH, or a -CH2OH group, at the respective location of one of the dashed lines there is either a single bond or a double bond, where if X is an OH group there is at least one double bond, as a fragrance and / or flavoring agent.
[0017] An alternative, particularly preferred alternative, is here and in the following, the use of a compound of formula (Ic), where X represents a -CHO, a -OH, or a -CH2OH group, at the respective location of one of the dashed lines there is either a single bond or a double bond, where if X is an OH group there is at least one double bond, as a fragrance and / or flavoring agent.
[0018] A particularly preferred alternative to formula (I), formula (1a), formula (Ib), and / or formula (Ic) is, here and in the following, that the double bond is a "C=C" double bond.
[0019] The use of the following molecular variants as fragrance and / or flavoring agents remains preferred:
[0020] The molecular variants are shown with the meta-substituent, but the substituent can also be preferentially bonded in the ortho- or para-position, as in: 4-isopentylcyclohex-2-en-1-ol, 2-isopentylcyclohex-2-en-1-ol, 4-isopentylcyclohex-2-en-1-one, or 2-isopentylcyclohex-2-en-1-one. Therefore, all the example formulas shown above are also preferred with the ortho- or para-substituent.
[0021] The compounds of formula (I), formula (1a), formula (Ib), and / or formula (Ic) possess unique olfactory properties that clearly distinguish them from, and even surpass, known odorants and / or flavorings. The suitability of these compounds as odorants and / or flavorings was previously unknown. It is therefore particularly surprising that these valuable odorants and / or flavorings with their interesting and complex olfactory properties have been discovered.
[0022] The use of the compounds according to the invention as rose fragrance and / or flavoring substances is particularly preferred.
[0023] A preferred embodiment of the present invention relates to the use of a compound of formula (I), formula (1a), formula (Ib), and / or formula (Ic), wherein X represents a -CHO, a -OH, or a -CH2OH group, and at least one double bond is present at the respective location of one of the dashed lines, as a fragrance and / or flavoring agent.
[0024] The use of the following molecular variants as fragrance and / or flavoring agents is particularly preferred:
[0025] The molecular variants are each preferably shown with the meta-substituent; the substituent can also preferably be bonded in the ortho- or para-position, as in: 4-isopentylcyclohex-2-en-1-ol, 2-isopentylcyclohex-2-en-1-ol, 4-isopentylcyclohex-2-en-1-one, or 2-isopentylcyclohex-2-en-1-one. All the example formulas shown above are therefore also preferred with the ortho- or para-substituent.
[0026] These compounds are particularly preferred because they exhibit a pronounced rosy and fruity odor profile. Additionally, they possess positive secondary properties, such as high stability under certain application conditions.
[0027] An alternative preferred embodiment of the present invention relates to compounds of formula (I), formula (1a), formula (Ib), and / or formula (Ic), wherein X represents a -CHO, a -OH, or a -CH2OH group, and a double bond is present at the respective location of one of the dashed lines in the ring and in the isobutyl side chain, as a fragrance and / or flavoring agent.
[0028] A further preferred embodiment of the present invention relates to compounds of formula (I), formula (1a), formula (Ib), and / or formula (Ic), wherein X represents a -CHO, a -OH, or a -CH2OH group, a single bond or a double bond is present at the location of one of the dashed lines, and wherein the compound is not 2-(3-methylbutyl)cyclohexan-1-ol, 2-(3-methylbutyl)cyclohexan-1-one, 3-(3-methylbutyl)cyclohexan-1-ol, 3-(3-methylbutyl)cyclohexan-1-one, 4-(3-methylbutyl)cyclohexan-1-ol, or 4-(3-methylbutyl)cyclohexan-1-one, as a fragrance and / or flavoring agent.
[0029] The use of the following molecular variants as fragrance and / or flavoring agents is particularly preferred:
[0030] The molecular variants are preferably shown with the meta-substituent; the substituent can also be bonded in the ortho- or para-position, as in: 4-isopentylcyclohex-2-en-1-ol, 2-isopentylcyclohex-2-en-1-ol, 4-isopentylcyclohex-2-en-1-one, or 2-isopentylcyclohex-2-en-1-one. All the example formulas shown above are therefore also preferred with the ortho- or para-substituent.
[0031] An alternative preferred embodiment of the present invention relates to compounds of formula (I), formula (1a), formula (Ib), and / or formula (Ic), wherein X represents a -CHO, a -OH, or a -CH2OH group, and a double bond is present at the respective location of one of the dashed lines, either in the ring or in the isobutyl side chain, as a fragrance and / or flavoring agent.
[0032] These compounds are particularly preferred because they can modify and / or enhance the fruity, floral and woody notes especially well.
[0033] The invention relates in a second aspect to compounds of formula (II), where X represents a -CHO or a -CH2OH group, a single bond or a double bond is present at the location of one of the dashed lines, and where the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, provided that if a double bond is present in the ring, then the 3-isopentyl or 3-isopent-2-enyl residue is directly bonded to this double bond as an ortho or meta substituent.
[0034] The preferred embodiments and structural variants of the first aspect of the present invention also apply to the second aspect and can also be combined analogously with the basic structure according to Formula II.
[0035] In this context, a further preferred embodiment of the present invention relates to the following molecular variants:
[0036] The compounds of formula (II) have an additional carbon atom between the ring and the heteroatom, making them particularly suitable as fragrances. Furthermore, the compounds according to the invention are distinguished by exceptionally good adhesion (long lasting) and high substantivity.
[0037] An alternative preferred embodiment of the present invention relates to compounds of formula (II), wherein X represents a -CHO or a -CH2OH group, a single bond is present at the location of the dashed lines, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, provided that if a double bond is present in the ring, then the 3-isopentyl or 3-isopent-2-enyl residue is directly bonded to this double bond as an ortho or meta substituent.
[0038] A preferred embodiment of the present invention relates to the use of a compound of formula (II), where X represents a -CHO or a -CH2OH group, a single bond or a double bond is present at the location of the dashed lines, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, provided that if a double bond is present in the ring, then the 3-isopentyl or 3-isopent-2-enyl residue is directly bonded to this double bond as an ortho or meta substituent, as a fragrance and / or flavoring agent.
[0039] The use of the following molecular variants as fragrance and / or flavoring agents is particularly preferred:
[0040] These molecular variants are each preferably shown with the meta-substituent; the substituent can also be bonded in the ortho- or para-position, as in: 2-isopentylcyclohex-2-ene-1-carbaldehyde, 4-isopentylcyclohex-2-ene-1-carbaldehyde, 2-(3-methylbut-2-enyl)cyclohexanecarbaldehyde, 4-(3-methylbut-2-enyl)cyclohexanecarbaldehyde, [2-(3-methylbut-2-enyl)cyclohexyl]methanol, [4-(3-methylbut-2-enyl)cyclohexyl]methanol, (2-isopentylcyclohex-2-ene-1-yl)methanol, or (4-isopentylcyclohex-2-ene-1-yl)methanol. All of the example formulas shown above are therefore also preferred with the ortho- or para-substituent.
[0041] The compounds of formula (II) possess an outstanding and unique odor profile, which includes, among other things, rosy and floral notes. Furthermore, the compounds according to the invention are distinguished by exceptionally good adhesion (long lasting) and high substantivity.
[0042] An alternative preferred embodiment of the present invention relates to compounds of formula (II), wherein X represents a -CHO or a -CH2OH group, a single bond is present at the location of the dashed lines, and the 3-isopentyl or 3-isopentenyl residue is connected to the X group on the ring in the ortho, meta, or para position, as a fragrance and / or flavoring agent.
[0043] The use of the following molecular variants as fragrance and / or flavoring agents is particularly preferred: 2-isopentylcyclohexanecarbaldehyde, (2-isopentylcyclohexyl)methanol, 3-isopentylcyclohexanecarbaldehyde, (3-isopentylcyclohexyl)methanol, 4-isopentylcyclohexanecarbaldehyde and (4-isopentyl-cyclohexyl)methanol.
[0044] These compounds are particularly preferred because they have odor-enhancing properties (so-called booster or enhancer effect) and / or, in combination with other fragrance and / or flavoring substances, round off their naturalness, freshness, fullness, (radiance) power and / or radiance.
[0045] Another alternative preferred embodiment of the present invention relates to the use of a compound of formula (II), wherein X represents a -CHO or a -CH2OH group, at least one double bond is present at the location of one of the dashed lines and the 3-isopentyl or 3-isopentenyl residue is connected to the X group on the ring in the ortho, meta, or para position, as a fragrance and / or flavoring agent.
[0046] The use of the following molecular variants as fragrance and / or flavoring agents is particularly preferred:
[0047] The molecular variants are preferably shown with the meta-substituent; the substituent can also be bonded in the ortho- or para-position, as in: 2-isopentylcyclohex-2-ene-1-carbaldehyde, 4-isopentylcyclohex-2-ene-1-carbaldehyde, 2-(3-methylbut-2-enyl)cyclohexanecarbaldehyde, 4-(3-methylbut-2-enyl)cyclohexanecarbaldehyde, [2-(3-methylbut-2-enyl)cyclohexyl]methanol, [4-(3-methylbut-2-enyl)cyclohexyl]methanol, (2-isopentylcyclohex-2-en-1-yl)methanol, or (4-isopentylcyclohex-2-en-1-yl)methanol. All of the example formulas shown above are therefore also preferred with the ortho- or para-substituent.
[0048] The compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to the invention or to be used according to the invention can be in any optically active form, as well as in any mixture of stereoisomers, for example as a diastereomeric mixture or as a racemate.
[0049] A preferred embodiment of the present invention relates to compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II), in all forms of their cis or trans isomers (E / Z isomers) at the 2-, 3-, or 4-position, as well as mixtures thereof.
[0050] In a third aspect, the invention relates to the use of a compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to variants according to the invention, as a rose-note fragrance.
[0051] In a fourth aspect, the invention relates to the use of a compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) for conveying, modifying, and / or enhancing one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic, and balsamic, preferably at least one of the notes green and / or fruity.
[0052] A preferred embodiment of the present invention relates to the use of a compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to variants of the invention for conveying one, two or more odor notes selected from the group consisting of the notes green, fresh, fruity and woody.
[0053] Preferably the present invention relates to the use of a compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to variants of the invention as a fragrance and / or flavoring agent, i) with a rose note and / or ii) for conveying, modifying and / or enhancing one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, woody, sweet, earthy, fatty, metallic and balsamic, wherein preferably at least one of the notes is conveyed, modified and / or enhanced as green and / or fruity.
[0054] In a fifth aspect, the invention relates to a fragrance and / or flavoring substance comprising at least one compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to variants according to the invention.
[0055] The compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) are particularly well-suited for use in fragrance and / or flavoring mixtures and / or compositions due to their olfactory properties. One or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) can be combined with a variety of other fragrance and / or flavoring substances and used in numerous different products and articles. The compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) can be combined particularly advantageously with other fragrance and / or flavoring substances in various proportions to form fragrance and / or flavoring mixtures and / or compositions according to the invention.
[0056] In a further embodiment, the invention relates to a fragrance and / or flavoring mixture comprising at least one fragrance and / or flavoring according to the fifth aspect and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, further comprising one or more additional fragrances and / or flavorings, wherein the additional or one, several or all of the fragrances and / or flavorings is / are selected from a group consisting of: extracts from natural raw materials, preferably essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures and / or individual fragrances, preferably from the group consisting of (1) hydrocarbons; (2) aliphatic alcohols; (3) aliphatic aldehydes and their acetals; (4) aliphatic ketones and their oximes; (5) Aliphatic sulfur-containing compounds; (6) Aliphatic nitriles; (7) Esters of aliphatic carboxylic acids;(8) Acyclic terpene alcohols; (9) Acyclic terpene aldehydes and ketones; (10) Cyclic terpene alcohols; (11) Cyclic terpene aldehydes and ketones; (12) Cyclic alcohols; (13) Cycloaliphatic alcohols; (14) Cyclic and cycloaliphatic ethers; (15) Cyclic and macrocyclic ketones; (16) Cycloaliphatic aldehydes; (17) Cycloaliphatic ketones; (18) Esters of cyclic alcohols; (19) Esters of cycloaliphatic alcohols; (20) Esters of cycloaliphatic carboxylic acids; (21) Araliphatic alcohols; (22) Esters of araliphatic alcohols and aliphatic carboxylic acids; (23) Araliphatic ethers; (24) Aromatic and araliphatic aldehydes; (25) Aromatic and araliphatic ketones; (26) Aromatic and araliphatic carboxylic acids and their esters; (27) Nitrogen-containing aromatic compounds; (28) Phenols, phenyl ethers and phenyl esters; (29) Heterocyclic compounds; (30) Lactones; and mixtures thereof.;
[0057] In a sixth aspect, the invention relates to a fragrance and / or flavoring mixture comprising at least one compound of formula (III), where X represents a -CHO, a -OH, or a -CH2OH group, a single bond or a double bond is present at the respective location of one of the dashed lines, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group and contains at least one other fragrance ingredient.
[0058] The compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) according to the invention or to be used according to the invention are usually used in a sensorially effective quantity, i.e. in a total quantity in which they have a sensory effect.
[0059] Preferably, the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol according to the invention or to be used according to the invention are used together with other fragrances.
[0060] Such fragrance and / or flavoring mixtures and / or compositions can be produced in the usual way, for example by simply mixing or homogenizing the components. These additional fragrance and / or flavoring substances can be any other fragrance and / or flavoring substances.
[0061] In a preferred fragrance and / or flavoring mixture and / or fragrance and / or flavoring composition according to the invention, the weight ratio of the total amount of compounds of formula (I), formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III), preferably in one of the embodiments specified above as preferred, to the total amount of further fragrance and / or flavoring substances is in the range of 1 : 1000 to 1 : 0.5.
[0062] In particular, by combining the compounds of the above-mentioned formulas, and especially formula (I) and formula (III), in variants according to the invention, preferably in one of the embodiments indicated as preferred, with one or more further odorants and / or flavorings (preferably with a woody, fruity, and / or floral odor or taste), interesting new odorant and / or flavoring mixtures and / or odorant and / or flavoring compositions can be produced. In this way, mixtures with particularly interesting, natural, new, and original notes can be created. Odorants and / or flavorings suitable as (b)-component, as described above, of an odorant and / or flavoring composition according to the invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vols. I and II, Montclair, NJ 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.
[0063] Specifically, the following should be mentioned: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as amber tincture; amyris oil; angelica seed oil; angelica root oil; anise oil; valerian oil; basil oil; treemoss absolute; bay oil; mugwort oil; benzoin oil; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calamus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassia absolute; castoreum absolute; cedar leaf oil; cedarwood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil; costus root oil; cumin oil; cypress oil; davana oil; dill herb oil; dill seed oil; Eau de brouts absolute; oakmoss absolute; elemi oil; tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; fennel oil; spruce needle oil; galbanum oil; galbanum resin; geranium oil; grapefruit oil; guaiac wood oil; Gurjun balm; Gurjun balsam oil; Helichrysum absolute; helichrysum oil; ginger oil; orris root absolute;Iris root oil; Jasmine absolute; Calamus oil; Blue chamomile oil; Roman chamomile oil; Carrot seed oil; Cascarilla oil; Pine needle oil; Spearmint oil; Caraway oil; Labdanum oil; Labdanum absolute; Labdanum resin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; Linaloe oil; Litsea cubeba oil; Bay leaf oil; Mace oil; Marjoram oil; Mandarin oil; Massoi bark oil; Mimosa absolute; Musk seed oil; Musk tincture; Clary sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Frankincense absolute; Frankincense oil; Opopanax oil; Orange blossom absolute; orange oil; oregano oil; palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil; peppermint oil; pepper oil; pimento oil; pine oil; poley oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spike lavender oil; star anise oil; styrax oil;Marigold oil; fir needle 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; wine yeast oil; wormwood oil; wintergreen oil; ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof or isolated components thereof;
[0064] Individual fragrance components from the group of hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; ( E , Z )-1,3,5-undecatriene; styrene; diphenylmethane; aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; ( E )-2-Hexenol; 1-Octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; ( E , Z)-2,6-Nonadienol; 3,7-Dimethyl-7-methoxyoctan-2-ol; 9-Decenol; 10-Undecenol; 4-Methyl-3-decen-5-ol; der aliphatischen Aldehyde und deren Acetale wie z.B. Hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; 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; Heptanaldiethylacetal; 1,1-Dimethoxy-2,2,5-trimethyl-4-hexen; Citronellyloxyacetaldehyd; 1-(1-Methoxy-propoxy)-( Z )-3-hexen; 1-(1-Methoxy-propoxy)-( E)-3-hexene; the 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; the aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol; the aliphatic nitriles such as 2-nonenonitrile; 2-Undecenonitrile; 2-Tridecenitrile; 3,12-Tridecadienitrile; 3,7-Dimethyl-2,6-octadienonitrile; 3,7-Dimethyl-6-octenonitrile; the ester of aliphatic carboxylic acids such as ( E )- and ( Z )-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; ( E )-2-Hexenyl acetate; ( E )- and ( Z)-3-Hexenylacetat; Octylacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat; Isoamylbutyrat; Hexylbutyrat; ( E )- und ( Z )-3-Hexenyl-isobutyrat; Hexylcrotonat; Ethylisovalerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat; Allylheptanoat; Ethyloctanoat; Ethyl-( E , Z)-2,4-decadienoate; methyl 2-octinate; methyl 2-noninate; allyl 2-isoamyloxyacetate; Methyl 3,7-dimethyl-2,6-octadiene oate; 4-methyl 2-pentyl crotonate; the acyclic terpene alcohols such as B. geraniol; Nerol; lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylene-7-octen-2-ol; 2,6-Dimethyl-5,7-octadien-2-ol; 2,6-Dimethyl-3,5-octadien-2-ol; 3,7-Dimethyl-4,6-octadien-3-ol; 3,7-Dimethyl-1,5,7-octatrien-3-ol 2,6-Dimethyl-2,5,7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; the acyclic terpene aldehydes and ketones such as citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranial acetone; and the dimethyl and diethyl acetals of geranial, neral, the cyclic terpene alcohols such as...Menthol; Isopulegol; α-Terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalool oxide; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoate; the cyclic terpene aldehydes and ketones such as menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-isomethylionone; β-isomethylionone; α-Iron; β-damascenone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-Hexa-hydro-1,1,5,5-tetramethyl-2. H -2,4a-methano-naphthalene-8(5 H )-one; 2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; Nootkatone; Dihydronootkatone; 4,6,8-Megastigmatrien-3-one; α-Sinensal; β-Sinensal; acetylated cedarwood oil (methylcedryl ketone); of the cyclic alcohols such as 4- tert-Butylcyclohexanol; 3,3,5-Trimethylcyclohexanol; 3-Isocamphylcyclohexanol; 2,6,9-Trimethyl- Z 2, Z 5, E 9-cyclododecatrien-1-ol; 2-Isobutyl-4-methyltetrahydro-2 H-pyran-4-ol; der cycloaliphatischen Alkohole wie z.B. 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; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-Trimethyl-cyclohexyl)pentan-3-ol; 1-(2,2,6-Trimethylcyclohexyl)hexan-3-ol; der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether; 1,1-Dimethoxycyclododecan; (Ethoxymethoxy)cyclo-dodecan; α-Cedrenepoxid; 3a,6,6,9a-Tetramethyldodecahydro-naphtho[2,1b]furan; 3a-Ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1b]fura; 1,5,9-Trimethyl-13-oxabi-cyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxan; der cyclischen und makrocyclischen Ketone wie z.B. 4- tert-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Pentyl-cyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2-penten-1-yl-2-cyclopenten-1-on; 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl-4-cyclopentadecenon; 3-Methyl-5-cyclopentadecenon; 3-Methylcyclopenta-decanon; 4-(1-Ethoxyvinyl)-3,3,5,5-tetra-methylcyclohexanon; 4- tert -Pentylcyclo-hexanon; 5-Cyclohexadecen-1-on; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5 H)-indanon; 8-Cyclohexadecen-1-on; 9-Cyclo-heptadecen-1-on; Cyclopentadecanon; Cyclohexadecanon; der cycloaliphatischen Aldehyde wie z.B. 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd; der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1-on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphta-lenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton; der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4 -tert- Butylcyclohexylacetat; 2- tert -Pentylcyclohexylacetat; 4- tert -Pentyl-cyclo-hexyl-acetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthylacetat; 2-Cyclo-pentylcyclopentylcrotonat; 3-Pentyltetrahydro-2 H-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; the esters of cycloaliphatic alcohols such as e.g., 1-cyclohexyl ethyl crotonate; the esters of cycloaliphatic carboxylic acids such as e.g., allyl-3-cyclohexyl propionate; allylcyclohexyl oxyacetate; cis - and trans -Methyldihydrojasmonate; cis - and trans-Methyljasmonat; Methyl-2-hexyl-3-oxocyclopentancarboxylat; Ethyl-2-ethyl-6,6-dimethyl-2-cyclohexencarboxylat; Ethyl-2,3,6,6-tetramethyl-2-cyclohexen-carboxylat; Ethyl-2-methyl-1,3-dioxolan-2-acetat; der araliphatischen Alkohole wie z.B. Benzylalkohol; 1-Phenylethylalkohol; 3-Phenylpropanol; 2-Phenylpropanol; 2-Phenoxyethanol; 2,2-Dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1,1-Dimethyl-2-phenylethylalkohol; 1,1-Dimethyl-3-phenylpropanol; 1-Ethyl-1-methyl-3-phenyl-propanol; 2-Methyl-5-phenyl-pentanol; 3-Methyl-5-phenylpentanol; 3-Phenyl-2-propen-1-ol; 4-Methoxybenzylalkohol; 1-(4-Isopropylphenyl)ethanol; der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B.Benzyl acetate; Benzyl propionate; Benzyl isobutyrate; Benzyl isovalerate; 2-Phenylethyl acetate; 2-Phenylethyl propionate; 2-Phenylethyl isobutyrate; 2-Phenyl ethyl isovalerate; 1-Phenylethyl acetate; α-Trichloromethylbenzyl acetate; α,α-Dimethylphenylethyl acetate; α,α-Dimethylphenylethyl butyrate; Cinnamyl acetate; 2-Phenoxyethyl isobutyrate; 4-Methoxybenzyl acetate; the araliphatic ethers such as 2-Phenylethyl methyl ether; 2-Phenylethyl isoamyl ether; 2-Phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethyl acetal; Phenylacetaldehyde diethyl acetal; Hydratropaaldehyde dimethyl acetal; Phenylacetaldehyde glycerol acetal; 2,4,6-Trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-Tetra-hydro-indeno[1,2-d]-m-dioxine; 4,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine; of the aromatic and araliphatic aldehydes such as e.g.Benzaldehyd; Phenylacetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4-Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4-isopropylphenyl)propanal; 2-Methyl-3-(4-isobutylphenyl)propanal; 3-(4-. tert -Butyl-phenyl)-propanal; Zimtaldehyd; α-Butylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5-phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenz-aldehyd; 4-Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4-methylendioxyphenyl)propanal; der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4-Methylacetophenon; 4-Methoxyacetophenon; 4- tert -Butyl-2,6-dimethylaceto-phenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1-(2-Naphtha-lenyl)ethanon;2-Benzofuranylethanon; (3-Methyl-2-benzofuranyl)ethanon; Benzophenon; 1,1,2,3,3,6-Hexamethyl-5-indanylmethylketon; 6- tert-Butyl-1,1-di-methyl-4-indanyl methyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1 H -5-indenyl]ethanone; 5',6',7',8'-Tetrahydro-3',5',5',6',8',8'-hexamethyl-2-aceto-naphthone; of aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methylphenyl acetate; ethylphenyl acetate; geranylphenyl acetate; phenylethylphenyl acetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allylphenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl 3-methyl-3-phenyl glycidate; of nitrogenous aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5- tert -butylbenzene; 3,5-Dinitro-2,6-dimethyl-4- tert-butylacetophenone; cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenonitrile; 3-methyl-5-phenylpentanonitrile; methyl anthranilate; methyl-N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4- tert -butyl-phenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6- sec- Butylquinoline; 2-(3-Phenylpropyl)pyridine; Indole; Skatole; 2-Methoxy-3-isopropylpyrazine; 2-Isobutyl-3-methoxypyrazine; of phenols, phenyl ethers and phenyl esters such as estragole; anethole; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; β-naphthyl methyl ether; β-naphthyl ethyl ether; β-naphthyl isobutyl ether; 1,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresylphenyl acetate; of heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2 H -furan-3-one; 2-Ethyl-4-hydroxy-5-methyl-2 H-furan-3-one; 3-Hydroxy-2-methyl-4 H -pyran-4-one; 2-Ethyl-3-hydroxy-4 H -pyran-4-one; the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decene-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; 1,16-Hexadeca-nolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexa-decanolide; 12-oxa-1,16-hexadecanolide; ethylene 1,12-dodecanedioate; ethylene 1,13-tridecanedioate; 2,3-dihydrocoumarin; Octahydrocoumarin.
[0065] In a seventh aspect, the present invention relates to a fragrance and / or flavoring composition comprising: (a) Component: one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) in variants according to the invention, and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, and (b) Component: one or more, preferably two, three, four, five, six, seven, eight, nine, ten or more, further fragrance and / or flavoring substances.
[0066] In a further variant, the present invention therefore relates to a fragrance and / or flavoring composition comprising: a) one or more compounds of formula (I) according to claims 1 to 3 and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or b) one or more, preferably two, three, four, five, six, seven, eight, nine, ten or more, further odorant and / or flavoring substances; (i) wherein the further odorant and / or flavoring substance(s) impart a woody, fruity and / or floral odor and / or taste, or (ii) wherein the further odorant and / or flavoring substance(s) impart a different odor.
[0067] In a preferred embodiment of a fragrance and / or flavoring composition according to the invention, the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II), and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol are preferably combined with one or more, particularly preferably with two, three, four, five or more, floral and / or fruity further fragrance and / or flavoring substances.
[0068] In a further preferred embodiment, the present invention relates to odor and / or flavor compositions and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, comprising one, two, three, four, five or more odor and / or flavor substances that impart a floral and / or fruity odor note.
[0069] The compound of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol advantageously (at least partially) enhances the odor of the floral fragrance and / or aroma substances according to the invention or to be used according to the invention.
[0070] Floral fragrance and / or flavoring substances with which the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol (particularly in fragrance and / or flavoring compositions according to the invention) can be advantageously combined, are preferably selected from the group consisting of: hydroxycitronellal, methoxycitronellal, cyclamenaldehyde [2-methyl-3-(4-isopropylphenyl)propanal], 1-(4-isopropyl-cyclohexyl)ethanol (Mugetanol®), 4-tert-butyl-α-methyldihydrocinnamaldehyde (Lilial®). cis-Hexahydrocuminyl alcohol (Mayol ®< ), 3-[4-(1,1-dimethylethyl)phenyl]propanal (Bourgeonal ®< ), 2,2-dimethyl-3-(3-methylphenyl)-propanol (Majantol ®< ), 3-methyl-3-(3-methylbenzyl)-butan-2-ol, 2-isobutyl-4-methyl-tetrahydro-2 H-pyran-4-ol (Florosa ®< ), 2-Methyl-3-(3,4-methylendioxyphenyl)propanal (Heliofolal ®< ), 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd (Lyral ®< ), 4-(Octahydro-4,7-methano-5 H -inden-5-yliden-butanal (Dupical ®< ), Vernaldehyd, 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd (Vertomugal ®< ), Octahydro-5-(4-methoxybutyliden)-4,7-methano-1 H-inden (Mugoflor ®< ), 2,6-Dimethyl-2-heptanol (Freesiol ®< ), 1-Ethyl-1-methyl-3-phenylpropanol (Phemec ®< ), 2,2-Dimethyl-3-phenyl-1-propanol (Muguet alcohol), Profarnesol, Dihydrofarnesol, Farnesol, Nerolidol, Hydroxycitronellaldimethylacetal, Hexylbenzoat, Geraniol, Nerol, Linalool, Tetrahydrogeraniol, Tetrahydrolinalool, Ethyllinalool, Geranyltiglinat, Phenethylalkohol (2-Phenylethylalkohol), Citronellol, Rosenoxid, 2-Methyl-5-phenylpentanol (Rosaphen), 3-Methyl-5-phenylpentanol (Phenoxanol), Methyldihydrojasmonat (Hedion ®< , Hedione ®< high cis), 2-Heptylcyclopentanon (Projasmon P), cis-Jasmon, Dihydrojasmon, Zimtalkohol (3-Phenyl-2-propen-1-ol), Dihydrozimtalkohol (3-Phenylpropanol), 2-Methyl-4-phenyl-1,3-dioxolan (Jacinthaflor ®< ) und Dihydromyrcenol (2,6-Dimethyl-7-octen-2-ol).
[0071] In an eighth aspect, the present invention relates to a fragrance and / or flavoring composition, wherein the further one or more fragrance and / or flavoring substances are selected from the group consisting of: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl 3-cyclohexyl propanoate, allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-dimethylbut-3-enyl 2-methylpropanoate, and / or (E)-1-(2,6,6-tri-methylcyclohex-2-en-1-yl)but-2-en-1-one.
[0072] In a preferred embodiment of a fragrance and / or flavoring composition according to the invention, the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol are preferably combined with one or more, particularly preferably with two, three, four, five or more further fragrance and / or flavoring substances, wherein the fragrance and / or flavoring substances are selected from the following group: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl 3-cyclohexyl propanoate. Allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-dimethylbut-3-enyl 2-methylpropanoate, (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one.
[0073] Furthermore, compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, which are to be used according to the invention, are advantageously suitable for enhancing the odor of, in particular, fruity fragrances and / or flavorings.
[0074] Fruity fragrance and / or flavoring substances with which the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol can be advantageously combined according to the invention, and which are therefore particularly preferred (further) fragrance and / or flavoring compositions according to the invention, are preferably selected from the group consisting of: 2-methylbutyric acid ethyl ester, 4-(p-hydroxyphenyl)-2-butanone, ethyl 3-methyl-3-phenylglycidate, isoamyl butyric acid ester, isoamyl acetate, n-butyl acetate, ethyl butyric acid ester, ethyl 3-methylbutyric acid ester, n-Hexanoic acid ethyl ester, n-Hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, γ-undecalactone, γ-nonalactone, hexanal3Z-Hexenal, n-Decanal, n-Dodecanal, Citral, Vanillin, Ethylvanillin, Maltol, Ethylmaltol and their mixtures.
[0075] In another variant, the weight ratio of the total amount of compounds of formula (I) or the aforementioned primary odorant to the total amount of other odorants and / or flavorings in the fragrance and / or flavoring composition is preferably in the range of 1:1000 to 1:0.5.
[0076] In a preferred fragrance and / or flavoring mixtures and / or compositions according to the invention, the total amount of compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol is in the range of 0.0001 to 99.9 wt.%, preferably in the range of 0.001 to 99.5 wt.%, particularly preferably in the range of 0.01 to 99 wt.%, in each case based on the total mass of the fragrance and / or flavoring mixtures and / or fragrance and / or flavoring compositions.
[0077] In further preferred fragrance and / or flavoring mixtures and / or fragrance and / or flavoring compositions according to the invention, the total amount of compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol is in the range of 0.01 to 90 wt.%, preferably in the range of 0.05 to 80 wt.%, more preferably in the range of 0.1 to 70 wt.%, particularly preferably in the range of 0.25 to 50 wt.%, especially preferably in the range of 0.5 to 40 wt.%, most preferably in the range of 0.75 to 25 wt.%, in each case based on the total mass of the fragrance and / or flavoring mixtures. and / or fragrance and / or flavor compositions.
[0078] In a preferred odorant and / or flavoring mixture and / or odorant and / or flavoring composition according to the invention, the total amount of the compound(s) of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) used in variants according to the invention is sufficient to modify, enhance and / or impart one or more of the aforementioned notes to the odor of the further odorant and / or flavoring substances in the direction of green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic and balsamic, preferably in the direction of green and / or fruity, preferably in the direction of rose.
[0079] If one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol are / are mainly used to impart more freshness, radiance, roundness, harmony and / or naturalness to a fragrance and / or flavoring mixture and / or fragrance and / or flavoring composition and / or to enhance certain notes (already present due to other fragrance or flavoring substances), the total amount of component (a) is preferably comparatively low and particularly preferably in the range of 0.01 to 5 wt.%, more preferably in the range of 0.1 to 2 wt.%, based on the total amount of the fragrance and / or flavoring mixture and / or fragrance and / or Aroma compositions.If a comparatively low concentration is chosen within the preferred concentration ranges, the characteristic odor notes mentioned above may not yet be conveyed in some cases, depending on the other components of the respective composition.
[0080] The preferred embodiments of the invention described above with regard to the uses according to the invention also apply accordingly to fragrance and / or flavoring mixtures and / or fragrance and / or flavoring compositions according to the invention, as well as perfumed articles according to the invention, in particular the information on preferred weight ratios.
[0081] The compound(s) of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to the invention, or to be used according to the invention, in particular the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II), and / or formula (III) characterized as preferred or particularly preferred within the scope of this invention, possess a very complex and diverse odor profile. This can otherwise usually only be achieved by mixtures of several components (such as essential oils or spice mixtures).
[0082] In addition to their primary, namely odorous, properties, the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) also possess positive secondary properties, in particular good adhesion and high substantivity compared to odor and / or flavoring substances with similar odor properties, as well as high stability in certain media and preparations and high yield.
[0083] In an eighth aspect, the invention relates to a method for modifying and / or enhancing (boosting) a scent with one, several or all of the fruity and / or woody notes and comprises the following steps: (a) Providing a compound of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) according to any one of the preceding claims 1 to 3 and / or one or more fragrance mixture(s) and / or composition(s) according to the invention; (b) Mixing a sensorially effective amount of this substance or these substances with a mixture of one or more fragrance and / or flavoring substances with one or more / all of the fruity and / or woody notes, sufficient to produce, sensorially modify and / or enhance a fruity and / or woody fragrance note in the finished preparation.
[0084] The compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol according to the invention or to be used according to the invention can also increase the intensity of an odorant and / or flavoring mixture according to the invention and round off the overall odor profile of the mixture and can be used to give an odorant and / or flavoring composition more fullness, freshness, (radiance), radiance, brilliance, rounding off, harmony and / or naturalness.
[0085] One or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol can be used in particular to impart freshness, radiance, roundness, harmony and / or naturalness to a fragrance and / or flavoring composition and / or to enhance existing odor notes.
[0086] In a ninth aspect, the present invention relates to the use of one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol for imparting a fragrance to hair and / or skin or to textile fibers (with regard to the odor notes preferably conveyed thereby, reference is made to the above descriptions), wherein the compound(s) of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-Methylbutyl)cyclohexan-1-ol is preferably used in combination with a surfactant or a surfactant mixture.
[0087] In a ninth aspect, the present invention relates to the use of the compounds of formula (I), formula (1a), formula (Ib), formula (Ic), formula (II) and / or formula (III) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol in odor and / or flavoring mixtures and / or odor and / or flavoring compositions according to the invention as an agent for increasing the substantivity and / or retention of an odor and / or flavoring mixture and / or odor and / or flavoring composition and / or as a fixative.
[0088] The sensory properties of compounds of formula (I) and their suitability as odorants and / or flavorings have not been described before and show surprising advantages, in particular an increased substantivity.
[0089] The following Table 1 contains the sensory, in particular olfactory, descriptions of some compounds of formula (I) according to the invention or to be used according to the invention.
[0090] The decisive factor here is always the structural formula of the compounds of formula (I) shown. Table 1 Nr.: structure Sensory description Substantivity 11 rosy, greasy, green good adhesion t 1 / 2 = 3d still smelling after 48h 12 rosy, green good adhesion t 1 / 2 = 3d still smelling after 48h 5 rosy, aldehydic, floral, green, citronellol Very good adhesion, t 1 / 2 = 3d, still smells strongly after 48h 6 intensely pink, of course Very good adhesion, t 1 / 2 = 3d, still smells strongly after 48h 7 aldehydic, floral, green Very good adhesion, t 1 / 2 = 3d, still smells strongly after 48h 8 Graphfrucht, rosy, fruity Very good adhesion, t 1 / 2 = 3d, still smells strongly after 48h 9 leathery, marine, graphite fruit, rhubarb, ozonic, floral, green Very good adhesion, t 1 / 2 = 3d, still smells strongly after 48h 10 floral, rosy, grassy Very good adhesion, t 1 / 2 = 3d, dry down after 48h still smells strongly.
[0091] Fragrance combinations or compositions remain particularly preferred. In particular, an extraordinary enhancement of the fruity note of some fragrances was achieved through combination with other secondary fragrances. Table 2 below contains the sensory, especially olfactory, descriptions of 4-(3-methylbutyl)cyclohexan-1-ol (Symrose) with secondary or combination fragrances. Table 2 Nr.: Secondary fuel name structure Dosage of Symrose with secondary tincture Odor mixture 21 Sultana 0,5-1 % softer, rounder, fruitier, less metallic 22 Apriflora 0,5-1 % Reduction of unpleasant fatty notes 23 Datelate 0,5-1 % More impact, drier, fruitier, leaning towards plum. 24 Buccoxime 0,5-1 % softer, rounder, less technical 25 Vertacetal Coeur 0,5-1 % less unpleasantly musty, more natural 26 Oxanthia 50% in TEC 0,5-1 % softer, rounder, fruitier, less metallic 27 Cassiffix 0,5-1 % stronger, fruitier, rounder and more natural 28 Amarocite 0,5-1 % more fruity and green, more natural 29 Isoamyl acetate 0,5-1 % softer, rounder, more natural, less metallic 30 Fragolane 0,5-1 % softer, rounder, less metallic 31 Ethyl Methyl Butyrate-2 0,5-1 % fruitier, rounder 32 Pyroprunate 0,5-1 % fruity-sweet, more ripe fruit 33 Cassix 150 0,5-1 % stronger, fruitier, rounder and more natural 34 Allylcyclohexyl propionate 0,5-1 % stronger, fruitier 35 Allyl capronate 0,5-1 % stronger, fruitier 36 Fruitinate 0,5-1 % More impact, juicier and fruitier, more natural 37 Isopentyrate 0,5-1 % More impact, more radiation, more natural, sweeter 38 Damascus Alpha 0,5-1 % softer, rounder, fruitier, less metallic
[0092] In a preferred embodiment, the invention relates to fragrance compositions and fragrance combinations comprising: one or more compounds of formula (I) according to embodiments of the invention and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and at least one fragrance and / or flavoring mixture in a sensorially effective amount, wherein the fragrance and / or flavoring mixture(s) is selected from the following group: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl 3-cyclohexyl propanoate, allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-Dimethylbut-3-enyl 2-methylpropanoate, and / or (E)-1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-en-1-one.
[0093] The combination of 4-(3-methylbutyl)cyclohexan-1-ol (Symrose) with other secondary odorants intensifies the perceived aroma. They often appear fruitier and more natural, thus acquiring a slightly modified character. Off-odors such as metallic notes are no longer perceived.
[0094] Preferably, Symrose or other compounds mentioned in the invention are combined with the following secondary pigments: Sultanene, Aprifloren, Datilat, Buccoxime, Vertacetal Coeur, Oxanthia 50% in TEC, Cassiffix, Amarocit, Fragolane, Pyroprunat, Cassix 150, Allylcyclohexylpropionate, Allylcaproate, Frutinate, Isopentyrate, Damascon alpha.
[0095] The following variants and basic odorants of the compounds 3-(3-methylbutyl)cyclohexan-1-one (2) or 3-(3-methylbutyl)cyclohexan-1-ol (3) also give, together with the secondary or combination odorants listed in Table 2, an intensified synergistic fruity odor, which partly already comes from the basic odorant but is particularly intensified by combination.
[0096] In a tenth aspect, the invention relates to perfumed or flavored articles, comprising: i) one or more compounds of formula (I) according to variants of the invention and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or an odorant and / or flavoring mixture and / or composition according to the invention in a sensorially effective amount, ii) one, two, three, four, five, six, seven, eight, nine, ten or more further odorant or flavoring substances, wherein preferably one, several or all of the further odorant substances impart a fruity and / or woody odor, iii) one or more further additives, excipients and / or active ingredients, preferably two, three, four, five or more additives, excipients and / or active ingredients. It is understood that the further additives, excipients and / or active ingredients are not odorants or flavoring substances.
[0097] In a preferred embodiment, the invention relates to perfumed or flavored articles comprising: one or more compounds of formula (I) according to variants of the invention and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and at least one fragrance and / or flavoring mixture in a sensorially effective amount, wherein the fragrance and / or flavoring mixture(s) is selected from the following group: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl 3-cyclohexyl propanoate, allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-Dimethylbut-3-enyl 2-methylpropanoate, and / or (E)-1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-en-1-one.
[0098] Additives, auxiliary substances and / or active ingredients which a perfumed or flavored article according to the invention may contain in addition to one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1- and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or a fragrance and / or flavoring mixture and / or fragrance and / or flavoring composition according to the invention (as defined below) are preferably selected from the group consisting of:
[0099] Preservatives, preferably those mentioned in US 2006 / 0089413, abrasives, anti-acne agents and sebum-reducing agents, preferably those mentioned in WO 2008 / 046791, anti-aging agents, preferably those mentioned in WO 2005 / 123101, antibacterial agents, anti-cellulite agents, anti-dandruff agents, preferably those mentioned in WO 2008 / 046795, anti-inflammatory agents, anti-irritant agents, anti-irritants (anti-inflammatory, anti-irritant and anti-irritant agents), preferably those mentioned in WO 2007 / 042472 and US 2006 / 0089413, antimicrobial agents, preferably those mentioned in WO 2005 / 123101, antioxidants, preferably those mentioned in WO 2005 / 123101, Astringents, antiseptics, antistatics, binders, buffers, carrier materials, preferably those mentioned in WO 2005 / 123101, chelating agents, preferably those mentioned in WO 2005 / 123101, cell stimulants, cleansing agents, conditioning agents, depilatory agents,surfactants, deodorizing agents and antiperspirants, preferably those mentioned in WO 2005 / 123101, plasticizers, emulsifiers, preferably those mentioned in WO 2005 / 123101, enzymes, essential oils, preferably those mentioned in US 2008 / 0070825, insect repellents, preferably those mentioned in WO 2005 / 123101, fibers, film formers, (other) fixatives, foaming agents, foam stabilizers, antifoaming agents, foam boosters, fungicides, gelling agents and gel-forming agents, preferably those mentioned in WO 2005 / 123101, hair conditioning agents, hair shaping agents, hair straightening agents, moisture regulators (moisturizing, moisturizing and / or humectant substances), preferably those mentioned in WO 2005 / 123101, osmolytes, preferably the compatible solutes mentioned in WO 2005 / 123101, preferably bleaching agents, strengthening agents, stain-removing agents, optical brightening agents mentioned in WO 01 / 76572 and WO 02 / 15686,Impregnating agents, dirt-repellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifying agents, plasticizing agents, covering agents, polishes, shine agents, polymers, preferably those mentioned in WO 2008 / 046676, powders, proteins and protein hydrolysates, preferably those mentioned in WO 2005 / 123101 and WO 2008 / 046676, emollient agents, abrasive agents, skin-soothing agents, skin-cleansing agents, skin-conditioning agents, skin-healing agents (skin repair agents), preferably containing cholesterol and / or fatty acids and / or ceramides and / or pseudoceramides, preferably those mentioned in WO 2006 / 053912, skin-lightening agents, preferably those mentioned in WO 2007 / 110415, skin-protecting agents, skin-emollient agents, skin-cooling agents, preferably those mentioned in WO skin-warming agents mentioned in WO 2005 / 123101, preferably the stabilizers, UV-absorbing agents and UV filters mentioned in WO 2005 / 123101,preferably the benzylidene β-dicarbonyl compounds mentioned in WO 2005 / 123101, preferably the α-benzoyl cinnamic acid nitriles mentioned in WO 2005 / 107692, preferably the AhR receptor antagonists mentioned in WO 2006 / 015954, preferably those mentioned in WO 2007 / 128723 and WO 2007 / 060256, detergents, fabric softeners, suspending agents, skin tanning agents, preferably those mentioned in WO 2006 / 045760, thickening agents, vitamins, preferably those mentioned in WO 2005 / 123101, fatty oils, waxes and fats, preferably those mentioned in WO 2005 / 123101, phospholipids, preferably those mentioned in WO 2005 / 123101, fatty acids (saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids), preferably those mentioned in WO 2005 / 123101, dyes and color-protecting agents as well as pigments, preferably those mentioned in WO 2005 / 123101, anti-corrosives, alcohols and polyols, preferably those mentioned in WO 2005 / 123101, surfactants,preferably those mentioned in WO 2005 / 123101, animal extracts, yeast extracts, extracts of algae or microalgae, electrolytes, liquefiers, organic solvents, preferably those mentioned in WO 2005 / 123101, hair growth modulating agents (hair growth promoting or hair growth inhibiting), preferably those mentioned in EP 2168570 and EP 2193785, or silicones and silicone derivatives, preferably those mentioned in WO 2008 / 046676.
[0100] A preferred embodiment of the present invention relates to perfumed or flavored articles, comprising one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or a fragrance and / or flavoring mixture and / or fragrance and / or flavoring composition, preferably in one of the embodiments specified above as preferred, in a sensorially effective amount sufficient to convey, modify, and / or enhance one or more of the odor notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic, and balsamic, preferably to convey and / or enhance one, two, three, four, five, six, seven, eight, nine, ten, or more further fragrance and / or flavoring substances, wherein preferably one, two, three, or more the other odor and / or aroma substances convey a woody, fruity and / or floral scent, two, three, four,five or more additives, excipients and / or active ingredients, wherein preferably one, two, three or more additives, excipients and / or active ingredients are selected from the group consisting of preservatives, inorganic salts, chelating agents, surfactants, skin and / or hair conditioning agents, enzymes, emulsifiers, fats, fatty oils, waxes, fatty alcohols, silicones, silicone derivatives and water.
[0101] Another preferred embodiment of the present invention relates to perfumed or flavored articles selected from the group consisting of washing and cleaning agents, hygiene or care products, in particular in the field of body and hair care, cosmetics and household.
[0102] Since a fragrance and / or flavoring composition according to the invention is suitable for perfuming or flavoring articles, the invention, in a further preferred embodiment, relates to a perfumed or flavored article comprising: an odorant composition according to the invention, preferably in one of the embodiments characterized as preferred, preferably in a sensorially effective amount, and one or more further additives, auxiliary and / or active ingredients, preferably two, three, four, five or more additives, auxiliary and / or active ingredients, preferably two, three, four, five or more of the additives, auxiliary and / or active ingredients indicated above as preferred.
[0103] An alternative preferred embodiment of the present invention relates to perfumed or flavored articles selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, fabric refreshers, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, decorative cosmetic products, candles, and lamp oils. Incense sticks, insecticides,Repellents and fuels.
[0104] Another preferred embodiment of the present invention relates to perfumed or flavored articles in which the total amount of compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or a fragrance and / or flavoring mixture and / or fragrance and / or flavoring composition according to the invention, preferably in one of the embodiments specified above as preferred, is in the range of 0.00001 to 10 wt.%, preferably in the range of 0.0001 to 5 wt.%, particularly preferably in the range of 0.001 to 2 wt.%, most preferably 0.005 to 1 wt.%, in each case based on the total mass of the perfumed or flavored article.
[0105] In an eleventh aspect, the invention relates to the use of a fragrance and / or flavoring composition according to the invention, preferably in one of the embodiments specified as preferred. (A) as a fragrance and / or flavoring composition (a) (i) with a rose note, and / or (ii) for conveying, modifying and / or enhancing one or more fragrance notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic and balsamic, preferably at least one of the notes green and / or fruity, and / or (b) (i) with a fruity and / or floral note, and / or (ii) for conveying, modifying and / or enhancing one or more fragrance and / or flavor notes selected from the group consisting of the notes woody, fruity and / or floral, and / or (c) with a floral, fruity, rose note and / or (B) as a component of a perfumed or flavored article.
[0106] Fragrance and / or flavor compositions according to the invention, which contain one or more compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, can be used for perfumery in liquid form, undiluted or diluted with a solvent. Preferred solvents for this purpose are ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, and diacetin.
[0107] Furthermore, fragrance and / or flavor compositions according to the invention, which contain compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, can be adsorbed onto a carrier material that ensures both a fine distribution of the fragrance and / or flavor substances in the product and a controlled release during application. Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as wood, cellulose-based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates, or polyurethanes. The combination of the composition and carrier material according to the invention represents an exemplary article according to the invention.
[0108] Fragrance and / or flavor compositions according to the invention, which contain compounds, can also be microencapsulated, spray-dried, as inclusion complexes or as extrusion products (i.e. articles according to the invention) and in this form can be added, for example, to a product to be perfumed.
[0109] If necessary, the properties of such modified compositions can be further optimized by so-called "coating" with suitable materials with a view to more targeted fragrance release, for which wax-like plastics such as polyvinyl alcohol are preferably used. The resulting products again constitute articles according to the invention.
[0110] The microencapsulation of the fragrance and / or flavor compositions according to the invention to form articles according to the invention can be carried out, for example, by the so-called coacervation process using capsule materials, e.g., made of polyurethane-like substances or soft gelatin. The spray-dried fragrance and / or flavor compositions can be produced, for example, by spray-drying an emulsion or dispersion containing the fragrance and / or flavor composition, wherein modified starches, proteins, dextrin, and vegetable gums can be used as carriers. Enclosure complexes can be produced, for example, by introducing dispersions of the fragrance and / or flavor composition and cyclodextrins or urea derivatives into a suitable solvent, e.g., water.Extrusion products can be obtained by fusing the fragrance and / or flavor compositions with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. isopropanol.
[0111] Compounds of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) and fragrance compositions according to the invention, which contain one or more compounds of formula (I) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, can be used in concentrated form, in solutions, or in the modified form described above for the production of perfumed or flavored articles according to the invention, such as perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, and perfumed refreshing wipes, as well as for the perfuming of acidic, alkaline, and neutral cleaning agents, such as...Floor cleaners, window cleaners, dishwashing liquids, bathroom and sanitary cleaners, scouring creams, solid and liquid toilet cleaners, powder and foam carpet cleaners, fabric refreshers, ironing aids, liquid detergents, powder detergents, laundry pretreatment products such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, as well as air fresheners in liquid, gel or solid form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe polishes, and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water type, such as...Skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products such as hairsprays, hair gels, firming hair lotions, hair conditioners, permanent and semi-permanent hair dyes, hair styling products such as cold waves and hair straightening products, hair tonics, hair creams and lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetic products such as eyeshadows, nail polishes, make-up, lipsticks, mascara, as well as candles, lamp oils, incense sticks, insecticides, repellents and fuels.
[0112] The spray-dried solid preparations according to the invention (as an example of articles according to the invention) are particularly well suited as semi-finished products for the manufacture of further preparations according to the invention. The spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of carrier substances, in particular maltodextrin and / or starch, and 5 to 40% by weight of excipients, preferably natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic.
[0113] In a twelfth aspect, the invention relates to a method for conveying, modifying and / or enhancing one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic and balsamic, preferably at least one of the notes green and / or fruity, preferably a rose note, comprising the following steps Providing one or more compounds of formula (I) as defined above, preferably in one of the embodiments specified above as preferred, or an inventive fragrance and / or flavoring composition as defined above, preferably in one of the embodiments specified above as preferred, providing an article, bringing the article into contact with a sensorially effective amount of the compound(s) of formula (I) or of the fragrance and / or flavoring composition as defined above.
[0114] A corresponding preferred method according to the invention is a method in which, after contact, (i) a perfumed or flavored article results or (ii) a product is produced from the product then present, which is selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, fabric refreshers, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants,Decorative cosmetics, candles, lamp oils, incense sticks, insecticides, repellents and fuels.
[0115] In a thirteenth aspect, the invention relates to a process for the preparation of a compound of formula (I), formula (1a), formula (Ib), formula (Ic), and / or formula (II) according to the invention or to be used according to the invention. The synthesis can be carried out using reactions and processes known per se. For example, the ketone (2) can be prepared from the commercially available compound 2-cyclohex-3-ene (compound 1) by means of a 1,4-Grignard reaction. The subsequent reduction of the ketone (2) yields the alcohol (3) (see Scheme 1 below).
[0116] The invention relates in a fourteenth aspect to a method for producing a compound (I) comprising at least steps (i), (ii) and (iii), characterized in that starting from 2-, or 3-, or 4-isopentylclohexanone by i) Wittig reaction yields 1-isopentyl-2-(methoxymethylene)cyclohexane (compound 4a), 1-isopentyl-3-(methoxymethylene)cyclohexane (compound 4b), or 1-isopentyl-4-(methoxymethylene)cyclohexane (compound 4c), ii) subsequent enol cleavage leads to the aldehyde (compound 5a, b, c), iii) and optional subsequent reduction yields the alcohol (compound 6a, b, c) (see Scheme 2 below).
[0117] The invention is explained in more detail below using examples. Unless otherwise stated, all specifications refer to weight.
[0118] Contrary to German spelling conventions, a period was used instead of a comma when specifying the number of decimal places.
[0119] Abbreviations used: DPG: Dipropylene glycol, TEC: Triethyl citrate, MTBE: Methyl tert-butyl ether, THF: Tetrahydrofuran, LAH: Lithium aluminum hydride, RT: Room temperature. Detailed description of the invention
[0120] The invention is described below with reference to exemplary embodiments. As explained in more detail below, the compounds of formula (I) according to the invention can be synthesized in the manner described below. It should also be noted that the IUPAC nomenclature may differ from the generic designation used previously. Example 1: 3-Isopentylcyclohexanone (2)
[0121] Preparation of the Grignard reagent: Lightly grind magnesium shavings (16.5 g, 0.687 mol) in a mortar and pestle, and place in 300 ml THF in a flask, add a spatula tip of iodine, heat under reflux (solution must decolorize), only then add 1 / 10 of 3-methylbutyl bromide (93.8 g, 0.621 mol) dropwise, after the formation of the Grignard reagent has begun, add the remaining 3-methylbutyl bromide dropwise to 150 ml THF, reflux the mixture for 1 h, and then allow the mixture to cool.
[0122] The Grignard solution is transferred via a cannula into a well-stirred suspension of copper iodide (8.0 g, 0.042 mol) in 300 ml THF, cooled to -5°C. After dissolving the copper iodide, allow to cool to -20°C and add cyclohex-2-en-1-one (34 g, 0.354 mol) dropwise. Stir at -20°C for 4 hours, then thaw at room temperature and stir overnight.
[0123] Work-up: Dissolve the mixture in 600 ml of ice-cold saturated ammonium chloride solution, add 300 ml of MTBE. Separate the phases, extract three times with 100 ml of MTBE, and wash the combined organic phases twice with 200 ml of saturated NaCl solution, dry, and concentrate. The crude product (60.0 g) was fractionally distilled under vacuum in a 15 cm Vigreux column. Yield: 52.0 g (87%) 1< H-NMR (400 MHz, CDCl 3 ) δ 2.42 (ddt, J = 13.8, 4.0, 1.9 Hz, 1H), 2.35 (dddt, J = 14.1, 5.0, 3.6, 1.5 Hz, 1H), 2.25 (dddd, J = 14.1, 12.2, 6.1, 1.2 Hz, 1H), 2.04 (dddd,J = 13.8, 8.0, 6.3, 3.9 Hz, 1H), 2.00 (ddt, J = 13.7, 11.6, 1.1 Hz, 1H), 1.96-1.84 (m, 1H), 1.79-1.70 (m, 1H), 1.70-1.58 (m, 1H), 1.50 (dp, J = 13.2, 6.6 Hz, 1H), 1.40-1.24 (m, 3H), 1.23-1.14 (m, 2H), 0.87 (d, J = 6.6 Hz, 6H); 13< C-NMR (101 MHz, CDCl 3 ) δ 212.16 (C=O), 48.31 (CH 2-ring ), 41.55 (CH 2-ring ), 39.38 (CH -ring ), 35.91 (CH 2 ), 34.35 (CH 2 ), 31.35 (CH 2-ring ), 28.08 ( C H-(CH 3 ) 2 , 25.32 (CH 2-ring ), 22.58 (CH-( C H 3 ) 2 , 22.57(CH-( C H 3 ) 2 . Example 2: 3-Isopentylcyclohexanol (3)
[0124] LAH (2.48 g, 0.065 mol) is placed in 200 ml of THF at room temperature. At 0–10 °C, the compound... 2 (10.0 g) carefully added to 70 ml THF. Stirred at room temperature for 30 minutes.
[0125] Processing :Add the mixture to 300 ml of ice water (exothermic, H₂ evolution). Add 150 ml of MTBE and then 150 ml of 25% sulfuric acid until the precipitate (Al(OH)₃) slowly dissolves. Separate the phases. Extract the aqueous phase twice with 50 ml of MTBE each time. Wash the combined organic phases once with 100 ml of sodium carbonate solution and once with 100 ml of saturated NaCl solution. Dry over Na₂SO₄ and concentrate. The crude product (10.0 g) is fractionally distilled using a Vigreux column under vacuum at 60 °C / 500-10 mbar. Yield: 9.5 g (94%) trans -Isomer: NMR: 1< H-NMR (400 MHz, CDCl 3 ) δ 4.09-4.01 (m, 1H), 1.78-1.57 (m, 5H), 1.56-1.45 (m, 3H), 1.25 (ddd, J = 13.3, 10.5, 2.9 Hz, 1H), 1.21-1.15 (m, 4H), 1.04-0.92 (m, 1H), 0.86 (d, J= 6.6 Hz, 6H) 13< C-NMR (101 MHz, CDCl 3 ) δ 67.08 (CH), 39.97 (CH 2 ), 36.41 (CH 2 ), 34.26 (CH 2 ), 33.61 (CH 2 ), 32.35 (CH 2 ), 31.97 (CH), 28.36 (CH), 22.81 (CH 3 ), 22.81 (CH 3 ), 20.21 (CH 2 ). cis -Isomer: NMR: 1< H-NMR (400 MHz, CDCl 3 ) δ 3.55 (tt, J = 10.8, 4.2 Hz, 1H), 2.03-1.93 (m, 2H), 1.76 (dp, J = 12.9, 3.2 Hz, 1H), 1.69-1.61 (m, 1H), 1.55-1.42 (m, J = 6.5 Hz, 1H), 1.33-1.17 (m, 6H), 1.16-1.07 (m, 1H), 0.93-0.83 (m, 1H), 0.87 (d, J = 6.6 Hz, 6H), 0.77 (tdd, J = 12.6, 10.9, 3.5 Hz, 1H) 13< C-NMR (101 MHz, CDCl 3 ) δ 71.14 (CH), 42.93 (CH 2 ), 36.90 (CH), 36.35 (CH 2 ), 36.06 (CH 2 ), 34.91(CH 2 ), 32.35 (CH 2 ), 28.36 (CH), 24.33 (CH 2 ), 22.83 (CH 3 ) 22.81 (CH 3 ). Example 3: (3 E / Z )-1-Isopentyl-3-(methoxymethylene)cyclohexane (4)
[0126] Methoxymethyltriphenylphosphoniumchlorid (84.2 g, 0.246 mol) in 500 ml THF vorlegen und auf 0 °C abkühlen lassen, Kalium- tertAdd butylate (112 g, 0.40 mol) in portions at 0 to 5 °C. Stir for 30 minutes, then slowly add 3-isopentylcyclohexanone (27.5 g, 0.164 mol) in 100 ml THF dropwise to the reaction solution, keeping the temperature below 10 °C. Stir for 30 minutes at < 10 °C, then slowly warm to room temperature over 22 hours.
[0127] Work-up: Quench the mixture with H₂O, extract three times with 1000 ml of ethyl acetate, wash the combined organic phases with 200 ml of saturated NaCl solution, dry, and concentrate (60 °C / 500-10 mbar). The crude product (96.2 g) was distilled on a bulb still (150 °C, 0.8 mbar). Yield: 36.2 g (quantitative) 1< H-NMR (400 MHz, CDCl 3 ) δ 5.75 (d, J = 1.7 Hz, 1H), 5.74 (t, J = 2.0 Hz, 1H), 3.53 (s, 6H), 2.75-2.67 (m, 1H), 2.66-2.59 (m, 1H), 2.06 (dt, J = 13.0, 2.3 Hz, 1H), 2.02-1.91 (m, 1H), 1.91-1.80 (m, 1H), 1.80-1.69 (m, 4H), 1.70-1.55 (m, 1H), 1.49 (dddd,J = 12.8, 10.4, 6.3, 2.6 Hz, 2H), 1.43 (s, 2H), 1.40-1.11 (m, 13H), 1.10-0.94 (m, 2H), 0.94-0.81 (m, 12H). 13< C-NMR (101 MHz, CDCl 3 ) δ 138.95, 138.94 isomer, 117.98, 117.93 isomer, 59.28, 59.28 isomer, 39.44 isomer, 38.21 isomer, 37.14, 37.43, 37.14 isomer, 36.27, 36.24 isomer, 34.68, 34.51 isomer, 33.19, 31.38, 28.32, 28.30 isomer, 28.25, 28.23 isomer, 26.93 isomer, 22.70, 22.67 isomer , 22.65, 22.63 isomer . Example 4: 3-isopentylcyclohexanecarbaldehyde (5)
[0128] Compound 4 (35.0 g, 0.178 mol) was placed in a 1l stirred tank in THF (400 ml) and 10% HCI solution (96 ml), then the reactants were added one after the other and the mixture was heated to boiling temperature, heated under reflux for 1h.
[0129] Work-up: Quench the mixture with water and extract three times with MTBE. Wash the combined organic phases once with water, dry, and evaporate (60 °C / 500–10 mbar). The crude product (31.0 g) was fractionally distilled under vacuum using a Vigreux column. Yield: 31.0 g (95%) trans -Isomer: NMR: 1< H-NMR (400 MHz, CDCl 3 ) δ 9.60 (d, J = 1.57 Hz, 1H), 2.23 (ttd, J = 12.17, 3.52, 1.62 Hz, 1H), 1.98 (mc , 3H), 1.75 (tq, J = 14.30, 3.34, 1.72 Hz, 1H), 1.71 (mc , 1H), 1.64 (mc , 3H), 1.20 (mc , 5H), 1.14 ( J = 3.70 Hz, 1H), 0.86 (d, J = 6.73 Hz, 6H). 13< C-NMR (101 MHz, CDCl 3 ) δ 204.83, 50.64, 37.13, 36.31, 36.05, 35.05, 33.58, 28.22, 26.12, 25.44, 22.63, 22.63. Example 5: (3-Isopentylcyclohexyl)methanol (6)
[0130] Under nitrogen (thoroughly rinse the apparatus), LAH (3.2 g, 0.085 mol) is placed in 200 ml of THF at room temperature. At 0-10 °C, 3-isopentylcyclohexanecarbaldehyde (14.0 g, 0.077 mol) is carefully added dropwise in 70 ml of THF. The mixture is stirred at room temperature for 30 minutes. Work-up: Add the mixture to 300 ml of ice water (exothermic, H₂ evolution). Add 150 ml of MTBE to the mixture, then add 150 ml of 25% sulfuric acid until the precipitate (Al(OH)₃) slowly dissolves. Separate the phases: extract the aqueous phase twice with 50 ml of MTBE each time, and the combined organic phases once with 100 ml of sodium carbonate solution and once with 100 ml of saturated NaCl solution. Wash, dry over Na₂SO₄, evaporate (60 °C / 500–10 mbar). The crude product (13.3 g) was distilled in a bulb still (90 °C, 1.0 mbar). Yield: 12.7 g (90%) 1< H-NMR (600 MHz, CDCl 3 ) δ 3.46 (dd, J = 10.5, 6.3 Hz, 1H), 3.44 (dd, J= 10.6, 6.3 Hz, 1H), 1.82-1.71 (m, 3H), 1.56-1.45 (m, 2H), 1.45-1.36 (m, 2H), 1.31-1.21 (m, 2H), 1.21-1.12 (m, 3H), 0.88 (d, J = 6.8 Hz, 1H), 0.86 (d, J = 6.6 Hz, 6H), 0.85-0.77 (m, 2H), 0.57 (q, J = 11.9 Hz, 1H); 13< C-NMR (151 MHz, CDCl 3 ) δ 68.93, 40.60, 37.50, 36.18, 35.46, 33.41, 32.77, 29.59, 28.54, 25.82, 22.71, 22.68. Example 6: 1-isopentyl cyclohexane carbaldehyde (7)
[0131] Analog zur Verbindung 3 wurde Verbindung 7 hergestellt.
[0132] 1H-NMR (400 MHz, CDCl3) δ 9.81 (d, J = 1.3 Hz, 1H), 9.55 (d, J = 4.0 Hz, 1H), 2.45 (dtd, J = 6.8, 3.9, 1.9 Hz, 1H), 2.01 (ddt, J = 10.0, 10.1, 3.9 Hz, 1H), 1.93 - 1.81 (m, 4H), 1.80 - 1.66 (m, 3H), 1.65 - 1.59 (m, 4H), 1.59 - 1.51 (m, 3H), 1.51 - 1.43 (m, 2H), 1.42 - 1.30 (m, 5H), 1.29 - 1.20 (m, 4H), 1.19 - 1.08 (m, 3H), 0.92 (d, J = 6.6 Hz, 3H), 0.87 (d, J = 6.6 Hz, 3H), 0.86 (d, J = 6.5 Hz, 3H), 0.84 (d, J = 6.5 Hz, 3H).
[0133] 13C-NMR (101 MHz, CDCl3) δ 206.13, 205.71, 70.63, 61.38, 55.81, 52.19, 51.07, 42.00, 41.96, 41.75, 37.26, 36.94, 36.72, 36.44, 35.70, 32.44, 30.34, 29.32, 28.73, 28.19, 28.14, 27.03, 26.52, 26.11, 25.27, 25.01, 24.77, 24.70, 24.21, 23.80, 23.69, 22.87, 22.71, 22.68, 22.62, 22.52, 22.28, 22.13. Example 7: (1-Isopentylcyclohexyl)methanol (8)
[0134] Analogous to connection 4, connection 8 was created from connection 7. Yield: > 90% 1H-NMR (400 MHz, CDCl3) δ 3.71 (dd, J = 10.8, 3.1 Hz, 1H), 3.67-3.58 (m, 3H), 1.871.64 (m, 9H), 1.64 - 1.44 (m, 5H), 1.04 - 1.29 (m, 18H), 0.84 - 0.89 (12H). 13C-NMR (101 MHz, CDCl3) δ 65.83, 63.35, 44.10, 42.09, 38.29, 37.08, 37.01, 35.57, 35.46, 31.57, 30.96, 29.59, 29.59, 28.83, 28.44, 28.30, 26.21, 25.97, 25.77, 23.01, 22.87, 22.87, 22.53, 22.37. Example 8: 4-isopentyl cyclohexane carbaldehyde (9)
[0135] Connection 9 was established analogously to connection 3.
[0136] 1H-NMR (400 MHz, CDCl3) δ 9.38 (s, 1H), 9.34 - 9.32 (m, 1H), 1.90 - 1.78 (m, 3H), 1.73 - 1.61 (m, 3H), 1.61 - 1.52 (m, 2H), 1.48 - 1.33 (m, 4H), 1.26 - 1.15 (m, 2H), 1.10 - 0.92 (m, 12H), 0.88 (d, J = 6.6Hz, 7H), 0.86 (d, J = 6.6 Hz, 7H), 0.68 - 0.53 (m, 2H).
[0137] 13C-NMR (101 MHz, CDCl3) δ 203.68, 202.89, 50.52, 47.39, 37.61, 36.95, 36.57, 36.48, 35.20, 34.12, 32.20, 32.20, 29.84, 29.84, 28.59, 28.54, 26.17, 26.17, 24.31, 24.31, 22.83, 22.83, 22.83, 22.83. Example 9: (4-Isopentylcyclohexyl)methanol (10)
[0138] Analogous to connection 4, connection 10 was created from connection 9. Yield: > 90% 1H-NMR (400 MHz, CDCl3) δ 3.44 (d, J = 6.3 Hz, 2H), 1.78 (d, J = 9.1 Hz, 4H), 1.48 (ddt, J = 11.4, 7.5, 4.5 Hz, 1H), 1.41 (dd, J = 10.8, 5.3 Hz, 1H), 1.17 (d, J = 3.1 Hz, 4H), 1.15 (d, J = 3.5 Hz, 1H), 0.98 - 0.88 (m, 5H), 0.86 (d, J = 6.6 Hz, 6H). 13C-NMR (101 MHz, CDCl3) δ 122.66, 68.83, 67.44, 66.47, 40.17, 38.44, 38.12, 36.77 36.32, 35.43, 35.11, 34.18, 33.82, 32.74, 31.83, 29.52, 28.97, 28.86, 28.28, 28.24, 25.76, 25.38, 22.70, 22.68. Example 10: Shampoo
[0139] The compound from Example 1 was incorporated into a shampoo base of the following composition at a dosage of 0.5 wt%: Sodium lauryl ether sulfate (e.g. Texapon NSO, Cognis Deutschland GmbH) 12% Cocamidopropyl betaine (e.g. Dehyton K, Cognis Deutschland GmbH) 2% Sodium chloride 1.4% Citric acid 1.3% Phenoxyethanol, methyl, ethyl, butyl and propyl paraben 0.5% Water 82.8%
[0140] The pH of the shampoo base was approximately 6. From this, 100 ml of a 20 wt% aqueous shampoo solution was prepared. Two strands of hair were washed together in this shampoo solution for 2 minutes and then rinsed for 20 seconds under lukewarm running water. One strand was wrapped wet in aluminum foil, and the second strand was dried with a hairdryer. Both strands were then assessed by a panel based on their odor. Odor description of both strands: intensely radiant, rose-like, fruity. Example 11: Fabric softener
[0141] The perfume composition from Example 2 (after the addition of 6 wt% of the ketone from Example 1) was incorporated into a fabric softener base of the following composition at a dosage of 0.5 wt%: Quarternary ammonium methosulfate (esterquat), approx. 90% (e.g. Rewoquat WE 18, Witco Surfactants GmbH) 5.5% Alkyldimethylbenzyl ammonium chloride, approx. 50% 0.2% (e.g. Preventol R50, Bayer AG) Color solution, approximately 1% 0.3% Water 94.0%
[0142] The pH of the fabric softener base was in the range of 2 to 3. Two fabric scraps were washed with 370 g of a 1% aqueous fabric softener solution (based on the fabric softener base, containing 0.5 wt% of the perfume composition from Example 2) in a line test machine using the fabric softener program for 30 minutes at 20 °C. The scraps were wrung out and then spun for 20 seconds. One scrap was vacuum-sealed while still wet, and the other was hung to dry. Both scraps were then odor-tested by a panel.
[0143] Scent description of both fabric scraps: floral, fresh, radiant and woody aspects with light fruity sweet undertones; rounded and harmonious scent impression. Example 12: Washing powder
[0144] The perfume oil composition from example 3 (after the addition of 1 wt%) was incorporated into a washing powder base of the following recipe at a dosage of 0.4 wt%: Linear Na alkyl benzene sulfonate 8.8 % Ethoxylated fatty alcohol C12-18 (7 EO) 4.7 % Sodium soap 3.2 % Defoamer DOW CORNING 2-4248S POWDERED ANTIFOAM, silicone oil on zeolite as carrier material 3.9 % Zeolite 4A 28.3 % Sodium carbonate 11.6 % Sodium salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2.4 % Sodium silicate 3.0 % Carboxymethylcellulose 1.2 % Dequest 2066 2.8 % ([[(Phosphonomethyl)imino]bis[(ethylenenitrilo)-bis(methylene)]]tetrakis-phosphonic acid, sodium salt) Optical brightener 0.2 % Sodium sulfate 6.5 % Protease 0.4 % Sodium perborate tetrahydrate 22.0 % Tetraacetylethylenediame in 1.0 %
[0145] Two fabric scraps were washed in a line test machine for 45 minutes at 60°C in the main wash cycle using 370 g of a 1% aqueous washing powder solution based on the 0.4 wt% perfume oil composition from Example 3 (the pH of the washing powder solution is clearly alkaline). The scraps were first rinsed for 5 minutes with cold water, wrung out, and then spun for 20 seconds. One scrap was vacuum-sealed while still wet, and the other was hung to dry. Both scraps were then olfactorily assessed by a panel.
[0146] Scent description: strong, radiant, rose-like with a natural note and fruity undertones; rounded and harmonious scent impression. Example 13: Perfume 1
[0147] IONONE BETA 50% DPG 25.00 FARENAL ® < 10% DPG 10.00 FLORAZON 1.00 HEXENOL CIS-3 1.00 Hexenyl acetate CIS-3 1.00 LIGUSTRAL 5.00 ALLYLAMYLGLYCOLATE 6.00 CYCLOGALBANATE ®< 6.00 MELONAL 10% DPG 6.00 DIHYDROMYRCENOL 32.00 LINALYL ACETATE 10.00 OXANTHIA 50% IN TEC 10% DPG 3.00 HEXYL ACETATE 25.00 ISOAMYL ACETATE 2.00 ETHYL BUTYRATE 2.00 Ethylcapronate 2.00 ALDEHYD C14 SOG 15.00 ALDEHYDE C18 SOG. 1.00 DECALACTON GAMMA 6.00 APPLE RED AROMABASE 4.00 ETHYLMETHYLBUTYRATE-2 5.00 MANZANATE 5.00 ALLYLCYCLOHEXYL PROPIONATE 5.00 ALLYLHEPTYLATE 7.00 PRUNELLA TYPE BASE 12.00 FRAMBINON ®< 10.00 Ethyl maltol 1% DPG 10.00 CYCLAMENALDEHYDE 5.00 CALONE 10% DPG 6.00 HELIONAL 45.00 FLORHYDRAL 2.50 FLOROSA 25.00 ETHYLLINALOOL 50.00 DIMETHYL BENZYLC CARBINYL ACETATE 8.00 TERPINEOL PURE 12.00 ROSE OXIDE 1.00 PHENYLETHYL ALCOHOL 56.00 Phenoxanol 15.00 SYMROSE ®< 1.00 DAMASCON ALPHA 1.00 DAMASCONE DELTA 1.00 BENZYL ACETATE 10.00 HEDION 140.00 AMYLSALICYLATE 65.00 UNDECAVERTOL 2.50 IONON ALPHA 10.00 ISOEUGENOL ACETATE 6.00 AGRUMEX LC 30.00 SANDRANOL ®< 6.00 EVERNYL 10% DPG 6.00 AMBROX DL 10% DPG 3.00 AMBRETTOLIDE 7.00 ETHYLENBRASSYLAT 95.00 GLOBALIDE ®< 50.00 INDOFLOR ®< KRIST. 10% DPG 5.00 DIPROPYLENGLYCOL 119.00 Beispiel 14: Parfum 2
[0148] ALKOHOL C 6 KOSCHER 6.00 OCTANON-3 0.50 HEXENOL CIS-3 12.00 HEXENYLACETAT CIS-3 8.00 VERTOCITRAL 8.00 CYCLOGALBANAT ®< 4.00 FLOROPAL 12.00 MAGNOLAN 10.00 MELONAL 4.00 DIHYDROMYRCENOL 40.00 CITRONITRIL 3.00 OXANTHIA 50% IN TEC 1.00 THYMOL KRIST. 4.00 HEXYLACETAT 40.00 ISOAMYLACETAT 100% 5.00 PRENYLACETAT 4.00 ETHYLBUTYRAT 5.00 EXOVERT HIGH IMPACT 10% DPG 2.00 ALDEHYD C14 SOG 15.00 DECALACTON GAMMA 5.00 ETHYLMETHYLBUTYRAT-2 5.00 MANZANATE 3.00 ALLYLCAPRONAT 5.00 ALLYLCYCLOHEXYLPROPIONAT 25.00 ALLYLHEPTYLAT 40.00 FRUITATE 4.00 ALDEHYD C16 SOG. 2.00 FRAMBINON ®< 10.00 MUGETANOL 10.00 CYCLOHEXYLMAGNOL 25.00 FREESIOL / CORPS 119 10.00 TETRAHYDROLINALOOL 190.00 DIMETHYLBENZYLCARBINYLACETAT 8.00 DIMETHYLBENZYLCARBINYLBUTYRAT 10.00 ROSENOXID 5.00 PHENIRAT ®< 30.00 SYMROSE ®< 115.00 DAMASCONE DELTA 3.00 ETHYLSAFRANAT 3.00 DELPHONE 1.00 VELOUTONE 2.00 NONADIENOL-2,6 1% DPG 8.00 UNDECAVERTOL 8.00 IRISNITRIL 10% DPG 3.00 AGRUMEX HC 120.00 ORYCLON SPEZIAL 165.00 HERBAFLORAT 30.00 RHUBOFIX 0.50 BRAHMANOL ®< 5.00 SANDRANOL ®< 45.00 SYNAMBRAN ®< R 50 % IN IPM 1.00 GLOBALIDE ®< 8.00 MACROLIDE ®< SUPRA 12.00 Beispiel 15: Parfum 3
[0149] FLOROPAL 1.50 MAGNOLAN 12.00 DIHYDROMYRCENOL 8.00 LINALYLACETAT 25.00 TERPINYLACETAT 12.00 CITRAL FF 10% DPG 2.00 CINEOL 1,4 10% DPG 2.00 ORANGE BASE COLIPA NEW 1.00 AMAROCIT ®< 14.00 TERPINOLEN DEXTRO 10% DPG 2.00 LAVENDER OEL CLONALE CENSO 2.00 EUCALYPTOL NAT. 6.00 CARDAMOM OIL RCO 0.80 MATE SUPERESSENCE 10% DPG 2.00 BORNEOL L / ISOBORNEOL 65 / 35 10% DPG 3.00 KAMPFER DL 10% IPM 12.00 SULTANENE ®< 1% DPG 5.00 HELIONAL 5.00 ETHYLLINALOOL 45.00 LINALOOLOXID 1.00 TETRAHYDROLINALOOL 35.00 DIMETHYLBENZYLCARBINYLBUTYRAT 1.00 TERPINEOL ALPHA 0.50 PHENYLETHYLACETAT 0.50 PHENYLETHYLALKOHOL 13.00 PHENOXANOL 3.00 SYMROSE ®< 1.00 DAMASCENON TOTAL 10% DPG 2.00 GIVESCONE 2.00 HEDION 220.00 JASMON CIS 10% DPG 8.00 METHYLOCTINCARBONAT 10% DPG 1.00 UNDECAVERTOL 3.00 ALLYLIONON 3.00 IONON ALPHA 12.00 IONON BETA 80.00 IRON ALPHA 2.00 HELIOTROPIN / PIPERONAL 4.00 COUMARONE 10% IPM 2.00 KOUMALACTONE 10% TEC 1% DPG 4.00 OCTAHYDROCUMARIN 4.00 TONKABOHNEN ABS. 10% DPG 6.00 TABANON 1% DPG 2.00 ISO E SUPER 80.00 GUAJAKHOLZOEL 10.00 GLOBALIDE ®< 20.00 MACROLIDE ®< SUPRA 2.00 GALAXOLID PURE 40.00 DIPROPYLENGLYCOL 128.70 Beispiel 16: Parfum 4
[0150] IONONE BETA REPL BY DPG 5.00 ESSIGSAEURE 1.00 ALDEHYD C10 1.00 ALDEHYD C11 UNDECANAL 0.50 ALDEHYD C12 LAURIN 3.00 HEXENOL CIS-3 5.00 HEXENYLACETAT CIS-3 5.00 VERTOCITRAL 5.00 VERTACETAL 0.50 STYROLYLACETAT 15.00 STYROLYLPROPIONAT 0.50 ISOPROPYLMETHYLTHIAZOL-2,4 10% DPG 1.00 MELONAL 10% DPG 2.00 DIHYDROMYRCENOL 25.00 CITRONENOEL ITAL. 5.00 ORANGENOEL 5.00 AMAROCIT ®< 25.00 CITRORANGE BASE COLIPA 5.00 MENTHOL L DEST. 1.00 ETHYLACETAT 2.00 HEXYLACETAT 5.00 ISOAMYLACETAT 100% 1.00 ISOBUTYLACETAT 10% DPG 2.00 JASMAPRUNAT 2.50 PRENYLACETAT 0.50 BUTYLBUTYRAT 2.00 HEXYLBUTYRAT 3.00 CAPRONSAEURE NAT. 1.00 ALDEHYD C14 SOG 15.00 DECALACTON GAMMA 2.00 ETHYLMETHYLBUTYRAT-2 1.50 SYMFRESH ®< NX 25.00 ALLYLCAPRONAT 5.00 ALLYLCYCLOHEXYLPROPIONAT 8.00 ALLYLHEPTYLAT 4.00 THIOMENTHANON-8,3 1% TEC 2.00 ETHYLMALTOL 5.00 PASSIONFRUIT TYPE BASE 25.00 MAJANTOL ®< 15.00 TETRAHYDROLINALOOL 50.00 DIMETHYLBENZYLCARBINYLACETAT 10.00 ROSENOXID L 1.00 SYMROSE ®< 15.00 DAMASCONE DELTA 2.00 BENZYLACETAT 15.00 HEDION 150.00 VELOUTONE 1.50 HEXYLSALICYLAT 15.00 UNDECAVERTOL 2.50 ISOEUGENOLACETAT 0.50 AGRUMEX LC 25.00 ORYCLON SPEZIAL 10.00 HERBYLPROPIONAT 2.00 SANDRANOL ®< 25.00 ETHYLENBRASSYLAT 25.00 GLOBALIDE ®< 25.00 DIPROPYLENGLYCOL 389.50 Beispiel 17: Parfum 5
[0151] IONONE BETA 50 % DPG 25.00 FARENAL ®< 10% DPG 10.00 FLORAZON 1.00 HEXENOL CIS-3 1.00 HEXENYLACETAT CIS-3 1.00 LIGUSTRAL 5.00 ALLYLAMYLGLYCOLAT 6.00 CYCLOGALBANAT ®< 6.00 MELONAL 10% DPG 6.00 DIHYDROMYRCENOL 32.00 LINALYLACETAT 10.00 OXANTHIA 50% IN TEC 10% DPG 3.00 HEXYLACETAT 25.00 ISOAMYLACETAT 2.00 ETHYLBUTYRAT 2.00 ETHYLCAPRONAT 2.00 ALDEHYD C14 SOG 15.00 ALDEHYD C18 SOG. 1.00 DECALACTON GAMMA 6.00 APPLE RED AROMABASE 4.00 ETHYLMETHYLBUTYRAT-2 5.00 MANZANATE 5.00 ALLYLCYCLOHEXYLPROPIONAT 5.00 ALLYLHEPTYLAT 7.00 PRUNELLA TYPE BASE 12.00 FRAMBINON ®< 10.00 ETHYLMALTOL 1% DPG 10.00 CYCLAMENALDEHYD 5.00 CALONE 10% DPG 6.00 HELIONAL 45.00 FLORHYDRAL 2.50 FLOROSA 25.00 ETHYLLINALOOL 50.00 DIMETHYLBENZYLCARBINYLACETAT 8.00 TERPINEOL REIN 12.00 AMAROCIT 1.00 PHENYLETHYLALKOHOL 56.00 PHENOXANOL 15.00 3-(3-Methylbutyl)cyclohexan-1-on (2) 1.00 DAMASCON ALPHA 1.00 DAMASCONE DELTA 1.00 BENZYLACETAT 10.00 HEDION 140.00 AMYLSALICYLAT 65.00 UNDECAVERTOL 2.50 IONON ALPHA 10.00 ISOEUGENOLACETAT 6.00 AGRUMEX LC 30.00 SANDRANOL ®< 6.00 EVERNYL 10% DPG 6.00 AMBROX DL 10% DPG 3.00 AMBRETTOLIDE 7.00 ETHYLENBRASSYLAT 95.00 GLOBALIDE ®< 50.00 INDOFLOR ®< KRIST. 10% DPG 5.00 DIPROPYLENGLYCOL 119.00 Beispiel 18: Parfum 6
[0152] IONONE BETA REPL BY DPG 5.00 ESSIGSAEURE 1.00 ALDEHYD C10 1.00 ALDEHYD C11 UNDECANAL 0.50 ALDEHYD C12 LAURIN 3.00 HEXENOL CIS-3 5.00 HEXENYLACETAT CIS-3 5.00 VERTOCITRAL 5.00 VERTACETAL 0.50 STYROLYLACETAT 15.00 STYROLYLPROPIONAT 0.50 ISOPROPYLMETHYLTHIAZOL-2,4 10% DPG 1.00 MELONAL 10% DPG 2.00 DIHYDROMYRCENOL 25.00 CITRONENOEL ITAL. 5.00 ORANGENOEL 5.00 AMAROCIT ®< 25.00 CITRORANGE BASE COLIPA 5.00 MENTHOL L DEST. 1.00 ETHYLACETAT 2.00 HEXYLACETAT 5.00 ISOAMYLACETAT 100% 1.00 ISOBUTYLACETAT 10% DPG 2.00 JASMAPRUNAT 2.50 PRENYLACETAT 0.50 BUTYLBUTYRAT 2.00 HEXYLBUTYRAT 3.00 CAPRONSAEURE NAT. 1.00 ALDEHYD C14 SOG 15.00 DECALACTON GAMMA 2.00 ETHYLMETHYLBUTYRAT-2 1.50 SYMFRESH ®< NX 25.00 ALLYLCAPRONAT 5.00 ALLYLCYCLOHEXYLPROPIONAT 8.00 ALLYLHEPTYLAT 4.00 THIOMENTHANON-8,3 1% TEC 2.00 ETHYLMALTOL 5.00 PASSIONFRUIT TYPE BASE 25.00 MAJANTOL ®< 15.00 TETRAHYDROLINALOOL 50.00 DIMETHYLBENZYLCARBINYLACETAT 10.00 DAMASCON ALPHA 1.00 3-(3-Methylbutyl)cyclohexan-1-on (2) 15.00 DAMASCONE DELTA 2.00 BENZYLACETAT 15.00 HEDION 150.00 VELOUTONE 1.50 HEXYLSALICYLAT 15.00 UNDECAVERTOL 2.50 ISOEUGENOLACETAT 0.50 AGRUMEX LC 25.00 ORYCLON SPEZIAL 10.00 HERBYLPROPIONAT 2.00 SANDRANOL ®< 25.00 ETHYLENBRASSYLAT 25.00 GLOBALIDE ®< 25.00 DIPROPYLENGLYCOL 389.50 Beispiel 19: Parfum 7
[0153] IONONE BETA REPL BY DPG 5.00 ESSIGSAEURE 1.00 ALDEHYD C10 1.00 ALDEHYD C11 UNDECANAL 0.50 ALDEHYD C12 LAURIN 3.00 HEXENOL CIS-3 5.00 HEXENYLACETAT CIS-3 5.00 VERTOCITRAL 5.00 VERTACETAL 0.50 STYROLYLACETAT 15.00 STYROLYLPROPIONAT 0.50 ISOPROPYLMETHYLTHIAZOL-2,4 10% DPG 1.00 MELONAL 10% DPG 2.00 DIHYDROMYRCENOL 25.00 CITRONENOEL ITAL. 5.00 ORANGENOEL 5.00 AMAROCIT ®< 25.00 CITRORANGE BASE COLIPA 5.00 MENTHOL L DEST. 1.00 ETHYLACETAT 2.00 HEXYLACETAT 5.00 ISOAMYLACETAT 100% 1.00 ISOBUTYLACETAT 10% DPG 2.00 JASMAPRUNAT 2.50 PRENYLACETAT 0.50 BUTYLBUTYRAT 2.00 HEXYLBUTYRAT 3.00 CAPRONSAEURE NAT. 1.00 ALDEHYD C14 SOG 15.00 DECALACTON GAMMA 2.00 ETHYLMETHYLBUTYRAT-2 1.50 SYMFRESH ®< NX 25.00 ALLYLCAPRONAT 5.00 ALLYLCYCLOHEXYLPROPIONAT 8.00 ALLYLHEPTYLAT 4.00 THIOMENTHANON-8,3 1% TEC 2.00 ETHYLMALTOL 5.00 PASSIONFRUIT TYPE BASE 25.00 MAJANTOL ®< 15.00 TETRAHYDROLINALOOL 50.00 DIMETHYLBENZYLCARBINYLACETAT 10.00 3-(3-Methylbutyl)cyclohexan-1-ol (3) 1.00 (4-ISOPENTYLCYCLOHEXYL)METHANOL 15.00 DAMASCONE DELTA 2.00 BENZYLACETAT 15.00 HEDION 150.00 VELOUTONE 1.50 HEXYLSALICYLAT 15.00 UNDECAVERTOL 2.50 ISOEUGENOLACETAT 0.50 AGRUMEX LC 25.00 ORYCLON SPEZIAL 10.00 HERBYLPROPIONAT 2.00 SANDRANOL ®< 25.00 ETHYLENBRASSYLAT 25.00 GLOBALIDE ®< 25.00 DIPROPYLENGLYCOL 389.50 Beispiel 20: Parfum 8
[0154] IONONE BETA 50 % DPG 25.00 FARENAL ®< 10% DPG 10.00 FLORAZON 1.00 HEXENOL CIS-3 1.00 HEXENYLACETAT CIS-3 1.00 LIGUSTRAL 5.00 ALLYLAMYLGLYCOLAT 6.00 CYCLOGALBANAT ®< 6.00 MELONAL 10% DPG 6.00 DIHYDROMYRCENOL 32.00 LINALYLACETAT 10.00 OXANTHIA 50% IN TEC 10% DPG 3.00 HEXYLACETAT 25.00 ISOAMYLACETAT 2.00 ETHYLBUTYRAT 2.00 ETHYLCAPRONAT 2.00 ALDEHYD C14 SOG 15.00 ALDEHYD C18 SOG. 1.00 DECALACTON GAMMA 6.00 APPLE RED AROMABASE 4.00 ETHYLMETHYLBUTYRAT-2 5.00 MANZANATE 5.00 ALLYLCYCLOHEXYLPROPIONAT 5.00 ALLYLHEPTYLAT 7.00 PRUNELLA TYPE BASE 12.00 FRAMBINON ®< 10.00 ETHYLMALTOL 1% DPG 10.00 CYCLAMENALDEHYD 5.00 CALONE 10% DPG 6.00 HELIONAL 45.00 FLORHYDRAL 2.50 FLOROSA 25.00 ETHYLLINALOOL 50.00 DIMETHYLBENZYLCARBINYLACETAT 8.00 TERPINEOL REIN 12.00 3-(3-Methylbutyl)cyclohexan-1-ol (3) 1.00 PHENYLETHYLALKOHOL 56.00 PHENOXANOL 15.00 (1-ISOPENTYLCYCLOHEXYL)METHANOL 1.00 DAMASCON ALPHA 1.00 DAMASCONE DELTA 1.00 BENZYLACETAT 10.00 HEDION 140.00 AMYLSALICYLAT 65.00 UNDECAVERTOL 2.50 IONON ALPHA 10.00 ISOEUGENOLACETAT 6.00 AGRUMEX LC 30.00 SANDRANOL ®< 6.00 EVERNYL 10% DPG 6.00 AMBROX DL 10% DPG 3.00 AMBRETTOLIDE 7.00 ETHYLENBRASSYLAT 95.00 GLOBALIDE ®< 50.00 INDOFLOR ®< KRIST. 10% DPG 5.00 DIPROPYLENGLYCOL 119.00
[0155] All perfume examples feature fruity scent blends. Perfume examples 5 to 8 are characterized by particularly pronounced fruit notes.
Claims
1. Use of a compound of Formula (1), wherein X represents a -CHO, -OH, or -CH2OH group, a single bond or a double bond is present at the location of each of the dashed lines, wherein if X = OH group, at least one double bond is present, and wherein the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, as a fragrance and / or flavoring agent.
2. Use of a compound of Formula (I) according to claim 1, wherein X represents a CHO, - OH, or -CH2OH group, and at least one double bond is present at the location of each of the dashed lines, as a fragrance and / or flavoring agent.
3. Use of a compound of Formula (I) according to claim 1, wherein X represents a CHO or a -CH2OH group, and a single bond or a double bond is present at the location of each of the dashed lines, as a fragrance and / or flavoring agent.
4. Use of a compound of Formula (I) according to claims 1 to 3 as a rose-note fragrance.
5. Use of a compound of Formula (I) according to claims 1 to 3 for conveying, modifying, and / or enhancing one, two, or more odor notes selected from the group consisting of green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, oily, metallic, and balsamic notes, preferably at least one of the notes being green and / or fruity.
6. A fragrance and / or flavoring agent comprising at least one compound of Formula (I) as defined in any one of claims 1 to 3.
7. Fragrance and / or flavoring mixture comprising at least one fragrance and / or flavoring agent according to claim 6, further comprising one or more additional fragrance and / or flavoring agents, wherein the additional or one, several or all of the fragrance and / or flavoring agents is / are selected from the group consisting of: extracts from natural raw materials, preferably essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures and / or individual fragrances, preferably from the group consisting of: (1) hydrocarbons; (2) aliphatic alcohols; (3) aliphatic aldehydes and their acetals; (4) aliphatic ketones and their oximes; (5) aliphatic sulfur-containing compounds; (6) aliphatic nitriles; (7) esters of aliphatic carboxylic acids; (8) acyclic terpene alcohols; (9) acyclic terpene aldehydes and ketones; (10) cyclic terpene alcohols; (11) Cyclic terpene aldehydes and ketones; (12) Cyclic alcohols; (13) Cycloaliphatic alcohols; (14) Cyclic and cycloaliphatic ethers; (15) Cyclic and macrocyclic ketones; (16) Cycloaliphatic aldehydes; (17) Cycloaliphatic ketones; (18) Esters of cyclic alcohols; (19) Esters of cycloaliphatic alcohols; (20) Esters of cycloaliphatic carboxylic acids; (21) Araliphatic alcohols; (22) Esters of araliphatic alcohols and aliphatic carboxylic acids; (23) Araliphatic ethers; (24) Aromatic and araliphatic aldehydes; (25) Aromatic and araliphatic ketones; (26) Aromatic and araliphatic carboxylic acids and their esters; (27) Nitrogen-containing aromatic compounds; (28) Phenols, phenyl ethers, and phenyl esters; (29) heterocyclic compounds; (30) lactones; and mixtures thereof.
8. Fragrance and / or flavoring composition comprising: (a) one or more compounds of Formula (I) according to claims 1 to 3 and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol, and (b) one or more, preferably two, three, four, five, six, seven, eight, nine, ten, or more, further fragrance and / or flavoring agents.
9. Fragrance and / or flavoring composition according to claim 8, wherein one or more further fragrance and / or flavoring agents are selected from the group consisting of: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl 3-cyclohexyl propanoate, allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-dimethylbut-3-enyl 2-methyl propanoate, and / or (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one.
10. Perfumed or flavored article comprising: - one or more compounds of Formula (I) according to claims 1 to 3 and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol and / or a fragrance and / or flavoring mixture according to claim 7 and / or a fragrance and / or flavoring composition according to claim 8 or 9 in a sensorially effective amount, - one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or flavoring substances, wherein preferably one, several or all of the further fragrance and / or flavoring substances impart a fruity and / or woody odor, - one or more further additives, excipients and / or active ingredients, preferably two, three, four, five or more additives, excipients and / or active ingredients.
11. Perfumed or flavored article according to claim 10, wherein the perfumed or flavored article is selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral detergents, fabric refreshers, ironing aids, liquid detergents, powdered detergents, laundry pre-treatments, fabric softeners, washing soaps, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, decorative cosmetic products, candles, Lamp oils, incense sticks, insecticides, repellents, and fuels.
12. Perfumed or flavored article according to claim 10 or 11, wherein the total amount of compounds of Formula (I) and / or 2-(3-methylbutyl)cyclohexan-1-ol and / or 3-(3-methylbutyl)cyclohexan-1-ol and / or 4-(3-methylbutyl)cyclohexan-1-ol is in the range of 0.00001 to 10 wt.%, preferably in the range of 0.0001 to 5 wt.%, particularly preferably in the range of 0.001 to 2 wt.%, most preferably 0.005 to 1 wt.%, in each case based on the total mass of the article.
13. Compounds of Formula (II) wherein X represents a -CHO or a -CH2OH group; and a single bond or a double bond is present at the location of each of the dashed lines, wherein the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, provided that if a double bond is present in the ring, then the 3-isopentyl or 3-isopent-2-enyl residue is directly bonded to this double bond as an ortho or meta substituent.
14. Compounds of Formula (I) according to claims 1 to 3 or of Formula (II) according to claim 13, wherein the compounds are present as a cis:trans isomer mixture at the 2-, 3-, or 4-position, with a predominant trans configuration.
15. A process for the preparation of a compound of Formula (II) according to claim 13 or 14, comprising at least steps (i), (ii), characterized in that, starting from 2-cyclohex-3-ene, (i) 1-isopentyl-2-(methoxymethylene)cyclohexane (compound 4a), 1-isopentyl-3-(methoxymethylene)cyclohexane (compound 4b), or 1-isopentyl-4-(methoxymethylene)cyclohexane (compound 4c) is obtained by Wittig-reaction. (ii) subsequent enol cleavage leads to the aldehyde (compound 5a, b, c); and (iii) the alcohol (compound 6a, b, c) is obtained by optional subsequent reduction.