Fragrance modifiers that impart an odor impression to a fragrance formulation
The compound of formula I, combined with fragrance and a non-aroma chemical carrier, enhances fragrance intensity and aroma impression by improving fragrance delivery, addressing the challenge of maintaining fragrance longevity and intensity in commercial products.
Patent Information
- Application Number
- PCT/US2025/033170
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-06-14
- Filing Date
- 2025-06-11
- Publication Date
- 2025-12-18
AI Technical Summary
Maintaining fragrance intensity and providing a consistent aroma impression over time is challenging in commercial fragrance products, as existing strategies often fail to effectively prolong the fragrance profile and intensity.
Incorporating a compound of formula I, where G is -O(O)C- or -C(O)O-, R1 is an unbranched or branched (C4-12)alkyl, R2 is a hydrogen or unbranched or branched (C1-6)alkyl or (C1-6)alkanol, and n is 1, 2, or 3, along with at least one fragrance and a non-aroma chemical carrier, enhances the aroma impression.
The compound of formula I significantly increases the perceived fragrance intensity, with at least 50% of panelists detecting an intense aroma impression when added to fragrance compositions.
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Figure US2025033170_18122025_PF_FP_ABST
Abstract
Description
[0001] FRAGRANCE MODIFIERS THAT IMPART AN ODOR IMPRESSION TO A
[0002] FRAGRANCE FORMULATION
[0003] BACKGROUND OF THE INVENTION
[0004] Maintaining a fragrance intensity and providing an aroma impression over time is key for a commercial fragrance consumer product, and therefore this has been a widely investigated field of research in fragrance design for several years. There are several approaches to solve the above-mentioned problem, in essence to make the fragrance profile last longer, more intense, and to impart the odor impression. Generally, these strategies center around the use of carrier and / or encapsulation materials to improve deposition of the fragrance delivery composition, around the proper selection of specific fragrance components, in essence fragrance components having a low(er) volatility, or around controlling the rate of release of the fragrance components, for example by using nonodorous fragrance fixatives or fragrance modulators.
[0005] It was surprisingly found that compounds of formula I impart an intense aroma impression to fragrance compositions relative to those that do not contain the compounds of formula I.
[0006] SUMMARY OF THE INVENTION
[0007] The present application discloses a composition comprising:
[0008] (i) a compound of formula I: wherein:
[0009] G is -O(O)C- or -C(O)O-, wherein the hyphens represent the points of attachment;
[0010] R1is an unbranched or branched (C4-12)alkyl ;
[0011] R2is a hydrogen, an unbranched or branched (Ci -e)al ky I or an unbranched or branched (Ci-e)alkanol; and n is independently 1 , 2, or 3;
[0012] (ii) at least one fragrance;
[0013] (iii) at least one of a non-aroma chemical carrier.
[0014] The present application discloses a method of imparting an intense aroma impression to a composition comprising at least one fragrance, comprising adding a composition comprising:
[0015] (i) a compound of formula I: wherein:
[0016] G is -O(O)C- or -0(0)0-, wherein the hyphens represent the points of attachment;
[0017] R1is an unbranched or branched (C4-12)alkyl ;
[0018] R2is a hydrogen, an unbranched or branched (Ci e)al ky I or an unbranched or branched (Ci-6)alkanol; and n is independently 1 , 2, or 3; to the composition, as determined according to the ASTM E1885-18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
[0019] The present application discloses a use of a compound of formula I: wherein:
[0020] G is -0(0)0- or -0(0)0-, wherein the hyphens represent the points of attachment;
[0021] R1is an unbranched or branched (C4-12)alkyl ;
[0022] R2is a hydrogen, an unbranched or branched (Ci -s)alkyl or an unbranched or branched (Ci-6)alkanol; and n is independently 1 , 2, or 3, to impart an intense aroma impression to a composition comprising at least one fragrance, as determined according to the ASTM E1885- 18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
[0023] DETAILED DESCRIPTION OF THE INVENTION
[0024] Definitions
[0025] “Fragrance modifier” means a compound that has the ability to modify the odor impression of a fragrance composition.
[0026] “Non-aroma chemical carrier” means a compound, mixture of compounds, or other additives that have no or no noteworthy olfactory sensory properties. Examples include surfactants, oil components, antioxidants, deodorant agents, and solvents. “Deodorant agent” is a compound or composition that counteract, mask, or eliminate odors on the body.
[0027] “Aroma” refers to a sensory property and comprises an odor and / or a flavor.
[0028] “Aroma chemical" means a substance which is used to obtain an odor impression and comprises its use to obtain a flavor impression.
[0029] “Odor impression” means a description of perceived odor, whether positive or negative. "Aroma impression" means an odor impression which is generally felt as pleasant or positive. “Intense aroma impression” means an aroma impression that is more elevated.
[0030] "Fragrance" means an aroma chemical, which predominately induces a pleasant or positive odor impression.
[0031] The present application discloses in a first aspect a composition comprising: (i) a compound of formula I wherein: G is -O(O)C- or
[0032] -C(O)O-, wherein the hyphens represent the points of attachment; R1is an unbranched or branched (C4-i2)alkyl; R2is a hydrogen, an unbranched or branched (Ci-e)alkyl or an unbranched or branched (Ci-e)alkanol; and n is independently 1 , 2, or 3; and (ii) at least one fragrance; and (iii) at least one of a non-aroma chemical carrier.
[0033] In one embodiment or in combination with any other embodiment disclosed herein, n is 1. In one embodiment or in combination with any other embodiment disclosed herein, n is 2. In one embodiment or in combination with any other embodiment disclosed herein, n is 3.
[0034] In one embodiment or in combination with any other embodiment disclosed herein, R2is hydrogen.
[0035] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkyl. In one class of this embodiment, R2is methyl, ethyl, or propyl. In one class of this embodiment, R2is methyl. In one class of this embodiment, R2is ethyl. In one class of this embodiment, R2is propyl.
[0036] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkanol. In one class of this embodiment, R2is -CH2-OH. In one class of this embodiment, R2is - CH2CH2-OH.
[0037] In one embodiment or in combination with any other embodiment disclosed herein, G is -O(O)C-.
[0038] In one class of this embodiment, R2is an unbranched or branched (Ci- e)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl.
[0039] In one class of this embodiment, R2is an unbranched or branched (C1- i2)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH.
[0040] In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethyl)pentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0041] In one subclass of this class, R1is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0042] In one embodiment or in combination with any other embodiment disclosed herein, G is -C(O)O-.
[0043] In one class of this embodiment, R2is an unbranched or branched (Ci- e)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl.
[0044] In one class of this embodiment, R2is an unbranched or branched (Ci- e)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH.
[0045] In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0046] In one subclass of this class, R1is is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0047] In one embodiment or in combination with any other embodiment, R1is an unbranched or branched (C4-i2)alkyl. In one class of this embodiment, R1is n-dodecyl-, n-decyl, n-nonyl, n-heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one class of this embodiment, R1is 2-ethylhexyl, n- octyl, 1 -ethylpentyl, or n-butyl. In one embodiment or in combination with any other embodiment disclosed herein, the compound of formula I is: (1 ) 2-ethylhexyl-3-hydrobutyrate 1 , (2) n-octyl-3-hydroxybutyrate 2, (3) 2,3-dihydroxylpropyl-2-ethylhexanoate 3, or (4) n-butyl-3-hydroxybutyrate 4.
[0048] In one embodiment or in combination with any other embodiment disclosed herein, the at least one non-aroma chemical carrier is a surfactant, an oil component, an antioxidant, a deodorant agent, a solvent, or combinations thereof.
[0049] In one embodiment or in combination with any other embodiment disclosed herein, the composition is a perfume composition, a body care composition, a hygiene article, a cleaning composition, a textile detergent, a scent composition, a food, a food supplement, a pharmaceutical composition, or a crop protection composition. In one class of this embodiment, the composition is a perfume composition. In one class of this embodiment, the composition is a body care composition. In one class of this embodiment, the composition is a hygiene article. In one class of this embodiment, the composition is a cleaning composition. In one class of this embodiment, the composition is a textile detergent. In one class of this embodiment, the composition is a scent composition. In one class of this embodiment, the composition is a food. In one class of this embodiment, the composition is a food supplement. In one class of this embodiment, the composition is a pharmaceutical composition. In one class of this embodiment, the composition is a crop protection composition.
[0050] In one embodiment or in combination with any other embodiment disclosed herein, when the composition is subjected to the ASTM E1885-18 test, at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
[0051] The present application discloses in a second aspect method of imparting an intense aroma impression to a composition comprising at least OH one fragrance, comprising adding a compound of formula I:1wherein: G is -O(O)C- or -C(O)O-, wherein the hyphens represent the points of attachment; R1is an unbranched or branched (C4-i2)alkyl; R2is a hydrogen, or an unbranched or branched (Ci-e)alkyl or an unbranched or branched (Ci- i2)alkanol; and n is independently 1 , 2, or 3, to the composition, as determined according to the ASTM E1885-18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
[0052] In one embodiment or in combination with any other embodiment disclosed herein, n is 1. In one embodiment or in combination with any other embodiment disclosed herein, n is 2. In one embodiment or in combination with any other embodiment disclosed herein, n is 3.
[0053] In one embodiment or in combination with any other embodiment disclosed herein, R2is hydrogen.
[0054] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkyl. In one class of this embodiment, R2is methyl, ethyl, or propyl. In one class of this embodiment, R2is methyl. In one class of this embodiment, R2is ethyl. In one class of this embodiment, R2is propyl.
[0055] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkanol. In one class of this embodiment, R2is -CH2-OH. In one class of this embodiment, R2is - CH2CH2-OH.
[0056] In one embodiment or in combination with any other embodiment disclosed herein, G is -O(O)C-.
[0057] In one class of this embodiment, R2is an unbranched or branched (C1- e)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl. In one class of this embodiment, R2is an unbranched or branched (Ci- e)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH.
[0058] In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0059] In one subclass of this class, R1is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0060] In one embodiment or in combination with any other embodiment disclosed herein, G is -C(O)O-.
[0061] In one class of this embodiment, R2is an unbranched or branched (C1- 6)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl.
[0062] In one class of this embodiment, R2is an unbranched or branched (C1- i2)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH.
[0063] In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0064] In one subclass of this class, R1is is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0065] In one embodiment or in combination with any other embodiment, R1is an unbranched or branched (C4-i2)alkyl. In one class of this embodiment, R1is n-dodecyl-, n-decyl, n-nonyl, n-heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one class of this embodiment, R1is 2-ethylhexyl, n- octyl, 1 -ethylpentyl, or n-butyl.
[0066] In one embodiment or in combination with any other embodiment disclosed herein, the compound of formula I is: (1 ) 2-ethylhexyl-3-hydrobutyrate 1 , (2) n-octyl-3-hydroxybutyrate 2, (3) 2,3-dihydroxylpropyl-2-ethylhexanoate 3, or (4) n-butyl-3-hydroxybutyrate 4.
[0067] In one embodiment or in combination with any other embodiment disclosed herein, the at least one non-aroma chemical carrier is a surfactant, an oil component, an antioxidant, a deodorant agent, a solvent, or combinations thereof.
[0068] In one embodiment or in combination with any other embodiment disclosed herein, the composition is a perfume composition, a body care composition, a hygiene article, a cleaning composition, a textile detergent, a scent composition, a food, a food supplement, a pharmaceutical composition, or a crop protection composition. In one class of this embodiment, the composition is a perfume composition. In one class of this embodiment, the composition is a body care composition. In one class of this embodiment, the composition is a hygiene article. In one class of this embodiment, the composition is a cleaning composition. In one class of this embodiment, the composition is a textile detergent. In one class of this embodiment, the composition is a scent composition. In one class of this embodiment, the composition is a food. In one class of this embodiment, the composition is a food supplement. In one class of this embodiment, the composition is a pharmaceutical composition. In one class of this embodiment, the composition is a crop protection composition. In one embodiment or in combination with any other embodiment disclosed herein, when the composition is subjected to the ASTM E1885-18 test, at least 50%, or at least 55%, or at least 60%, or at least 65%, or at least 70%, or at least 75%, or at least 80% of the panelists can detect an intense odor impression relative to a modified composition without the compound of formula I.
[0069] The present application discloses in a third aspect a use of a compound
[0070] OH of formula I:1, wherein: G is -O(O)C- or -C(O)O-, wherein the hyphens represent the points of attachment; R1is an unbranched or branched (C4-i2)alkyl; R2is a hydrogen, an unbranched or branched (Ci-e)alkyl or an unbranched or branched (Ci-e)alkanol; and n is independently 1 , 2, or 3, to impart an intense aroma impression to a composition comprising at least one fragrance, as determined according to the ASTM E1885-18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
[0071] In one embodiment or in combination with any other embodiment disclosed herein, n is 1. In one embodiment or in combination with any other embodiment disclosed herein, n is 2. In one embodiment or in combination with any other embodiment disclosed herein, n is 3.
[0072] In one embodiment or in combination with any other embodiment disclosed herein, R2is hydrogen.
[0073] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkyl. In one class of this embodiment, R2is methyl, ethyl, or propyl. In one class of this embodiment, R2is methyl. In one class of this embodiment, R2is ethyl. In one class of this embodiment, R2is propyl.
[0074] In one embodiment or in combination with any other embodiment disclosed herein, R2is an unbranched or branched (Ci-e)alkanol. In one class of this embodiment, R2is -CH2-OH. In one class of this embodiment, R2is - CH2CH2-OH.
[0075] In one embodiment or in combination with any other embodiment disclosed herein, G is -0(0)0.
[0076] In one class of this embodiment, R2is an unbranched or branched (C1- e)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl.
[0077] In one class of this embodiment, R2is an unbranched or branched (C1- e)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH.
[0078] In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0079] In one subclass of this class, R1is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0080] In one embodiment or in combination with any other embodiment disclosed herein, G is -C(0)0-.
[0081] In one class of this embodiment, R2is an unbranched or branched (C1- 6)alkyl. In one subclass of this class, R2is methyl, ethyl, or propyl. In one subclass of this class, R2is methyl. In one subclass of this class, R2is ethyl. In one subclass of this class, R2is propyl.
[0082] In one class of this embodiment, R2is an unbranched or branched (C1- 6)alkanol. In one subclass of this class, R2is -CH2-OH or -CH2CH2-OH. In one subclass of this class, R2is -CH2-OH. In one subclass of this class, R2is - CH2CH2-OH. In one class of this embodiment, R1is an unbranched or branched (C4- i2)alkyl. In one subclass of this class, R1is n-dodecyl-, n-decyl, n-nonyl, n- heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one sub-subclass of this subclass, n is 1 . In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0083] In one subclass of this class, R1is -CH2(CH2)2CH3, - CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3. In one sub-subclass of this subclass, n is 1. In one sub-subclass of this subclass, n is 2. In one sub-subclass of this subclass, n is 3.
[0084] In one embodiment or in combination with any other embodiment, R1is an unbranched or branched (C4-i2)alkyl. In one class of this embodiment, R1is n-dodecyl-, n-decyl, n-nonyl, n-heptyl, n-hexyl, n-pentyl, 2-ethylhexyl, n-octyl, 1 -ethylpentyl, or n-butyl. In one class of this embodiment, R1is 2-ethylhexyl, n- octyl, 1 -ethylpentyl, or n-butyl.
[0085] In one embodiment or in combination with any other embodiment disclosed herein, the compound of formula I is: (1 ) 2-ethylhexyl-3-hydrobutyrate 1 , (2) n-octyl-3-hydroxybutyrate 2, (3) 2,3-dihydroxylpropyl-2-ethylhexanoate 3, or (4) n-butyl-3-hydroxybutyrate 4.
[0086] In one embodiment or in combination with any other embodiment disclosed herein, the at least one non-aroma chemical carrier is a surfactant, an oil component, an antioxidant, a deodorant agent, a solvent, or combinations thereof.
[0087] In one embodiment or in combination with any other embodiment disclosed herein, the composition is a perfume composition, a body care composition, a hygiene article, a cleaning composition, a textile detergent, a scent composition, a food, a food supplement, a pharmaceutical composition, or a crop protection composition. In one class of this embodiment, the composition is a perfume composition. In one class of this embodiment, the composition is a body care composition. In one class of this embodiment, the composition is a hygiene article. In one class of this embodiment, the composition is a cleaning composition. In one class of this embodiment, the composition is a textile detergent. In one class of this embodiment, the composition is a scent composition. In one class of this embodiment, the composition is a food. In one class of this embodiment, the composition is a food supplement. In one class of this embodiment, the composition is a pharmaceutical composition. In one class of this embodiment, the composition is a crop protection composition.
[0088] In one embodiment or in combination with any other embodiment disclosed herein, when the composition is subjected to the ASTM E1885-18 test, at least 50%, or at least 55%, or at least 60%, or at least 65%, or at least 70%, or at least 75%, or at least 80% of the panelists can detect an intense odor impression relative to a modified composition without the compound of formula I.
[0089] Fragrances
[0090] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the at least one fragrance is geranyl acetate, alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, 4, 6, 6, 7,8,8- hexamethyl-1 ,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyllinalool, benzyl salicylate, 2-methyl-3-(4-tert- butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a- hexahydro-5-indenyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6- indenyl acetate, citronellol, citronel lyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styrolyl acetate, octahydro-2, 3, 8, 8-tetramethyl-2-acetonaphthone and / or 2-acetyl-1 ,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tertbutylcyclohexyl acetate, alphaionone, n-alpha-methylionone, alpha-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3- cyclohexenecarboxaldehyde, alpha-amylcinnamaldehyde, ethylene brassylate, (E)- and / or (Z)-3-methylcyclopentadec-5-enone, 15-pentadec-11 -enolide and / or 15-pentadec-12-enolide, 15-cyclopentadecanolide, 1-(5, 6,7,8- tetrahydro-3, 5, 5, 6, 8, 8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4- methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1 -yl)- 2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6- nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2, 4,4,7- tetramethyloct-6-en-3-one, 2,6-dimethyl-5-hepten-1-al, borneol, 3-(3- isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3- (4-ethyl phenyl)-2,2-dimethylpropanal, 7-methyl-2H-1 ,5-benzodioxepin-3(4H)- one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1 , 2, 3, 4, 4a, 5,6,7- octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2- methylpentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b- tetrahydroindeno[1 ,2-d][1 ,3]dioxine, (2-tert-butylcyclohexyl) acetate, or 3- [5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.
[0091] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the at least one fragrance is methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl- 4-methyltetrahydro-2H-pyran-4-ol, linalool, or 2-isobutyl-4-methyltetrahydro- 2H-pyran-4-ol,.
[0092] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the at least one fragrance is ethylvanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol), or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).
[0093] Further fragrances with which can be used in combination with the compound of formula I can be found, e.g., in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N. J., 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th Ed., Wiley-VCH, Weinheim 2001. Specifically, mention may be made of: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as e.g. ambergris tincture; amyris oil; angelica seed oil; angelica root oil; aniseed oil; valerian oil; basil oil; tree moss absolute; bay oil; mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calmus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassia absolute; castoreum absolute; cedar leaf oil; cedar wood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil; costus root oil; cumin oil; cypress oil; davana oil; dill weed oil; dill seed oil; Eau de brouts absolute; oak moss absolute; elemi oil; tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; fennel oil; pine needle oil; galbanum oil; galbanum resin; geranium oil; grapefruit oil; guaiacwood oil; gurjun balsam; gurjun balsam oil; helichrysum absolute; helichrysum oil; ginger oil; iris root absolute; iris root oil; jasmine absolute; calmus oil; camomile oil blue; roman camomile 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; lime oil distilled; lime oil pressed; linalool oil; Litsea cubeba oil; laurel leaf oil; mace oil; marjoram oil; mandarin oil; massoia 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; olibanum absolute; olibanum oil; opopanax oil; orange blossom absolute; orange oil; origanum oil; palmarosa oil; patchouli oil; perilla oil; peru balsam oil; parsley leaf oil; parsley seed oil; petitgrain oil; peppermint oil; pepper oil; pimento oil; pine oil; pennyroyal oil; rose absolute; rose wood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spike-lavender oil; star anise oil; styrax oil; tagetes oil; fir needle oil; tea tree oil; turpentine oil; thyme oil; tolubalsam; tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; wine lees oil; wormwood oil; winter green oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof, or ingredients isolated therefrom; individual fragrances from the group of hydrocarbons, such as e.g. 3 carene; alpha-pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p- cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1 ,3,5-undecatriene; styrene; diphenylmethane; the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6- dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 1 octen-3-ol; 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; the aliphatic aldehydes and acetals thereof such as e.g. hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2- methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5- heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6, 10-trimethyl-9- undecenal; 2,6,10 trimethyl-5,9-undecadienal; heptanal diethylacetal; 1 ,1- dimethoxy-2,2,5 trimethyl-4-hexene; citronellyloxyacetaldehyde; (E / Z)-1-(1- methoxypropoxy)-hex-3-ene; the aliphatic ketones and oximes thereof such as e.g. 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 e.g. 3- methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3- mercaptohexyl acetate; 3- mercapto hexyl butyrate; 3-acetylthiohexyl acetate; 1- menthene-8-thiol; the aliphatic nitriles such as e.g. 2-nonenenitrile; 2-undecenenitrile; 2 tridecenenitrile; 3, 12-tridecadienenitrile; 3,7-dimethyl-2,6-octadienenitrile; 3,7- dimethyl-6 octenenitrile; the esters of aliphatic carboxylic acids such as e.g. (E) and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5- trimethylhexyl acetate; 3 methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E) and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E) and (Z)-3- hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2- methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octinate; methyl 2-noninate; allyl 2-isoamyloxy acetate; methyl-3,7-dimethyl-2,6- octadienoate; 4-methyl-2-pentyl crotonate; the acyclic terpene alcohols such as e.g. geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; 2,6-dimethyl-7-octen-2-ol;
[0094] 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;
[0095] 3.7-dimethyl-1 ,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-1-ol; and the formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2 butenoates thereof; the acyclic terpene aldehydes and ketones such as e.g. geranial; neral; citronellal; 7 hydroxy-3, 7-dimethyloctanal; 7 methoxy-3,7-dimethyloctanal; 2,6, 10-trimethyl-9 undecenal; geranyl acetone; as well as the dimethyl and diethylacetals of geranial, neral, 7-hydroxy-3, 7-dimethyloctanal; the cyclic terpene alcohols such as e.g. menthol; isopulegol; alphaterpineol; terpine-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guajol; and the formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3- methyl-2-butenoates thereof; the cyclic terpene aldehydes and ketones such as e.g. menthone; isomenthone; 8 mercaptomenthan-3-one; carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n- methylionone; alpha-isomethylionone; beta-isomethylionone; alphairone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gammadamascone; 1 -(2,4,4-trimethyl-2-cyclohexen-1 -yl)-2-buten-1 -one; 1 ,3,4,6,7,8a-hexahydro-1 ,1 ,5,5-tetramethyl-2H-2,4a-methano-'inaphthalene- 8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal; beta-sinensal; acetylated cedar wood oil (methyl cedryl ketone); the cyclic alcohols such as e.g. 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3- isocamphylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2- isobutyl-4-methyltetrahydro-2H-pyran-4-ol; the cycloaliphatic alcohols such as e.g. alpha-3, 3- trimethylcyclohexylmethanol; 1 (4-isopropylcyclohexyl)ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-methyl-4-(2,2,3 trimethyl-3- cyclopent-1-yl)-2-buten-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3 cyclopent-1 -yl)-2- buten-1-ol; 3-methyl-5-(2,2,3 trimethyl-3-cyclopent-1-yl)pentan-2 ol; 3-methyl- 5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3- trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-trimethylcyclohexyl)pentan- 3-ol; 1 -(2,2,6-trimethylcyclohexyl) hexan-3-ol; the cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; cyclododecyl methyl ether; 1 ,1 -dimethoxycyclododecane; (ethoxymethoxy)cyclo-dodecane; alphacedrene epoxide; 3a, 6, 6,9a- tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a- trimethyldodecahydro-naphtho[2,1 -b]furan; 1 ,5,9-trimethyl-13-oxabicyclo-
[0096] [10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5- methyl-5-(1 -methylpropyl)-1 ,3-dioxane; the cyclic and macrocyclic ketones such as e.g. 4-tert- butylcyclohexanone; 2,2,5 trimethyl-5-pentylcyclopentanone; 2- heptylcyclopentanone; 2-pentylcyclo-pentanone; 2-hydroxy-3-methyl-2- cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2 cyclopenten-1-one; 3-methyl- 2-pentyl-2-cyclopenten-1 -one; 3-methyl-4-cyclopenta-decenone; 3-methyl-5- cyclopentadecenone; 3-methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3, 3,5,5- tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1 - one; 6,7-dihydro-1 ,1 ,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclo-hexadecen-1- one; 7-cyclohexadecen-1-one; (7 / 8)-cyclohexadecen-1-one; 9 cyclo- heptadecen-1-one; cyclopentadecanone; cyclohexadecanone; the cycloaliphatic aldehydes such as e.g. 2,4-dimethyl-3- cyclohexenecarbaldehyde; 2 methyl-4-(2,2,6-trimethylcyclohexen-1 -y l)-2- butenal; 4-(4-hydroxy-4-methylpentyl)-3 cyclohexene carbaldehyde; 4-(4- methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde; the cycloaliphatic ketones such as e.g. 1-(3,3-dimethylcyclohexyl)-4- penten-1 -one; 2,2 dimethyl-1 -(2, 4-dimethyl-3-cyclohexen-1 -yl)-1 -propanone; 1-(5,5-dimethyl-1 cyclo-hexen-1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl- 1 ,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl 2,6,10- trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl (2,4-dimethyl-3- cyclohexen-1-yl) ketone; the esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexyl acetate; 4-tertbutylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert- pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2- naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H- pyran-4-yl acetate; decahydro-2, 5, 5, 8a-tetramethyl-2-naphthyl acetate; 4,7- methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methano- 3a,4,5,6,7,7a-hexahydro-5 or 6 indenyl propionate; 4,7-methano-3a,4,5,6,7,7a- hexahydro-5 or 6-indenyl isobutyrate; 4,7 methanooctahydro-5 or 6-indenyl acetate; the esters of cycloaliphatic alcohols such as e.g. 1 -cyclohexylethyl crotonate; the esters of cycloaliphatic carboxylic acids such as e.g. allyl 3- cyclohexylpropionate; allyl cyclohexyloxyacetate; cis and trans-methyl dihydrojasmonate; cis and trans-methyl jasmonate; methyl 2-hexyl-3- oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6 dimethyl-2- cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2 cyclohexene-carboxylate; ethyl 2-methyl-1 ,3-dioxolane-2-acetate; the araliphatic alcohols such as e.g. benzyl alcohol; 1 -phenylethyl alcohol, 2 phenylethyl alcohol, 3-phenylpropanol; 2-phenylpropanol; 2- phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3- methylphenyl)propanol; 1 , 1 -dimethyl-2 phenylethyl alcohol; 1 , 1 -dimethyl-3- phenylpropanol; 1 -ethyl-1-methyl-3-phenylpropanol; 2-methyl-5- phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4- methoxy benzyl alcohol; 1-(4-isopropylphenyl)ethanol; the esters of araliphatic alcohols and aliphatic carboxylic acids such as e.g. benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2 phenylethyl isovalerate; 1 phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha, alphadimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4- methoxybenzyl acetate; the araliphatic ethers such as e.g. 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-tetrahydroindeno[1 ,2-d]-m-dioxine; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1 ,2-d]-m dioxine; the aromatic and araliphatic aldehydes such as e.g. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropaaldehyde; 4- methylbenzaldehyde; 4 methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2- dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert- butylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4- tertbutylphenyl)propanal; cinnamaldehyde; alpha-butylcinnamaldehyde; alphaamylcinnamaldehyde; alpha-hexylcinnamaldehyde; 3 methyl-5- phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3 methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4- methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4- methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal; the aromatic and araliphatic ketones such as e.g. acetophenone; 4- methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylaceto- phenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2- naphthalenyl)-ethanone; 2-benzofuranylethanone; (3-methyl-2- benzofuranyl)ethanone; benzophenone; 1 ,1 ,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1 , 1 dimethyl-4 indanyl methyl ketone; 1-[2,3- dihydro-1 , 1 ,2, 6-tetramethyl-3-(1-methylethyl)-1 H-5 indeny]ethanone; 5',6',7',8'- tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetonaphthone; the aromatic and araliphatic carboxylic acids and esters thereof such as e g. benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate; the nitrogen-containing aromatic compounds such as e.g. 2,4,6-trinitro- 1 ,3-dimethyl-5 tertbutylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert- butylacetophenone; cinnamonitrile; 3 methyl-5-phenyl-2-pentenonitrile; 3- methyl-5-phenylpentanonitrile; methyl anthranilate; methyl-N- methylanthranilate; Schiff bases of methyl anthranilate with 7 hydroxy-3, 7- dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4 dimethyl-3- cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec- butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy-3 isopropyl-pyrazine; 2-isobutyl-3-methoxypyrazine; the phenols, phenyl ethers and phenyl esters such as e.g. estragole; anethole; eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1 ,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2 ethoxy-5-(1-propenyl)phenol; p-cresyl phenylacetate; the heterocyclic compounds such as e.g. 2,5-dimethyl-4-hydroxy-2H- furan-3-one; 2 ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl- 4H-pyran-4-one; 2 ethyl-3-hydroxy-4H-pyran-4-one; the lactones such as e.g. 1 ,4-octanolide; 3-methyl-1 ,4-octanolide; 1 ,4- nonanolide; 1 ,4-decanolide; 8-decen-1 ,4-olide; 1 ,4-undecanolide; 1 ,4- dodecanolide; 1 ,5-decanolide; 1 ,5-dodecanolide; 4-methyl-1 ,4-decanolide; 1 ,15-pentadecanolide; cis and trans-11-pentadecen-1 , 15-olide; cis and trans- 12-pentadecen-1 , 15-olide; 1 ,16-hexadecanolide; 9-hexadecen-1 , 16-olide; 10- oxa-1 , 16-hexadecanolide; 11 -oxa-1 , 16-hexadecanolide; 12-oxa-1 , 16- hexadecanolide; ethylene 1 , 12-dodecanedioate; ethylene 1 ,13- tridecanedioate; coumarin; 2,3-dihydrocoumarin; octahydrocoumarin.
[0097] Solvents
[0098] In the context of the presently claimed invention, a “solvent” serves for the dilution of the compound of formula (I) to be used according to the invention and / or any further component of the composition without having its own aroma.
[0099] The amount of solvent(s) is selected depending on the composition.
[0100] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the solvent is selected from the group consisting of water, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, triethyl citrate and isopropyl myristate.
[0101] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the solvent is present in the composition in an amount of 0.01 wt% to 99.0 wt%, or 0.05 wt% to 95.0 wt%, or 0.1 wt% to 80.0 wt%, or 0.1 wt% to 70.0 wt%, or 0.1 wt% to 60.0 wt%, based on the total weight of the composition.
[0102] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the composition comprises 0.05 wt% to 10 wt%, or 0.1 wt% to 5 wt%, or 0.2 wt% to 3 wt% solvent(s), based on the total weight of the composition. In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the composition comprises 20 wt% to 70 wt%, or 25 wt% to 50 wt% of solvent(s), based on the total weight of the composition. Oil Component
[0103] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the oil component is present in an amount of 0.1 to 80 wt%, or 0.5 to 70 wt%, or 1 to 60 wt%, or 1 to 50 wt%, or 1 to 40 wt%, or 5 to 25 wt% or 5 to 15 wt%, based on the total weight of the composition.
[0104] The oil component may be Guerbet alcohols based on fatty alcohols containing 6 to 18, or 8 to 10, carbon atoms and other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate or erucyl erucate. Also suitable are esters of C18-C38 alkylhydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, or dioctyl malate, esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer dial or trimer triol), triglycerides based on C6-C10 fatty acids, liquid mono-, di- and triglyceride mixtures based on C6-C18 fatty acids, esters of C6-C22 fatty alcohols or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates such as, for example, dicaprylyl carbonate (Cetiol® CC), Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, esters of benzoic acid with linear and / or branched C6 to C22 alcohols (for example Finsov® TN), linear or branched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group such as, for example, dicaprylyl ether (Cetiol® OE), ring opening products of epoxidized fatty acid esters with polyols or hydrocarbons or mixtures thereof.
[0105] Antioxidants
[0106] It is to be understood that antioxidants are able to inhibit or prevent the undesired changes in the compositions to be protected caused by oxygen effects and other oxidative processes. The effect of the anti-oxidants consists in most cases in them acting as free-radical scavengers for the free radicals which arise during autoxidation.
[0107] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the antioxidant is amino acids (for example glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) or derivatives thereof; imidazoles (e.g. urocanic acid) or derivatives thereof; peptides, such as D,L-carnosine, D- carnosine, L-carnosine (=p-Alanyl-L-histidin) or derivatives thereof; carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene, lutein) or derivatives thereof; chlorogenic acid or derivatives thereof; lipoic acid or derivatives thereof (for example dihydrolipoic acid); auro-thioglucose, propylthiouracil and other thiols (for example thioredoxin, glutathione, cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters thereof) or salts thereof; dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides or salts); sulfoximine compounds (for example buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta- , hexa-, heptathionine sulfoximine); (metal) chelating agents (e.g. alphahydroxy fatty acids, palmitic acid, phytic acid, lactoferrin); alpha-hydroxy acids (for example citric acid, lactic acid, malic acid); humic acid, bile acid, bile extracts, bilirubin, biliverdin, boldin (=alkaloid from the plant Peumus boldus, boldo extract); EDTA, EGTA or derivatives thereof; unsaturated fatty acids or derivatives thereof (e.g. gamma-linolenic acid, linoleic acid, oleic acid); folic acid or derivatives thereof; ubiquinone and ubiquinol or derivatives thereof; vitamin C or derivatives (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate); tocopherols or derivatives (for example vitamin E acetate); vitamin A or derivatives (for example vitamin A palmitate); coniferyl benzoate of gum benzoin, rutic acid and derivatives thereof, alphaglycosylrutin, ferulic acid, furfurylideneglucitol; butylhydroxytoluene (BHT), butylhydroxyanisole (BHA); nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid or derivatives thereof, mannose or derivatives thereof; superoxide dismutase; zinc or derivatives thereof (for example ZnO, ZnSO4); selenium or derivatives thereof (for example selenomethionine); or stilbenes or derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide).
[0108] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the antioxidant is pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate or tocopherol.
[0109] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the compositions according to the presently claimed invention can comprise the antioxidant in an amount of 0.001 to 25 wt%, or 0.005 to 10 wt%, or 0.01 to 8 wt%, or 0.025 to 7 wt%, or 0.05 to 5 wt%, based on the total weight of the composition. Deodorant Agent
[0110] Deodorant agent counteract, mask or eliminate body odors. Body odors are formed through the action of skin bacteria on apocrine perspiration which results in the formation of unpleasant-smelling degradation products.
[0111] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the deodorant agent is an anti-perspirant, an esterase inhibitor, or an antibacterial agent.
[0112] A suitable deodorant agent is a salt of aluminum, zirconium or zinc. Examples include aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and complex compounds thereof, for example with 1 ,2-propylene glycol, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and complex compounds thereof, for example with amino acids, such as glycine. Aluminum chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and complex compounds thereof are examples.
[0113] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the deodorant agent is aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxyallantoinate, aluminum chloride tartrate, aluminum zirconium tri ch loro hydrate, aluminum zirconium tetrachlorohydrate, or aluminum zirconium pentachlorohydrate.
[0114] Where perspiration is present in on the body, extracellular enzymes- esterases, mainly proteases and / or lipases are formed by bacteria and split the esters present in the perspiration, releasing odors in the process. Suitable esterase inhibitors are for example trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate. Esterase inhibitors inhibit enzyme activity and thus reduce odor formation. The free acid is probably released by the cleavage of the citric acid ester and reduces the pH value of the skin to such an extent that the enzymes are inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, or zinc glycinate.
[0115] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the esterase inhibitor is trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester, or zinc glycinate.
[0116] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the esterase inhibitor in the range of 0.01 to 20 wt%, or 0.1 to 10 wt%, or 0.5 to 5 wt%, based on the total weight of the composition.
[0117] Surfactant
[0118] In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the surfactant is an anionic, a non-ionic, a cationic, an amphoteric or a zwitterionic surfactant. In one class of this embodiment, the surfactant is an anionic surfactant.
[0119] Surfactant-containing compositions, such as for example shower gels, foam baths, shampoos, etc., preferably contain at least one anionic surfactant. In one embodiment or in combination with any other embodiment, class, subclass, or sub-subclass in aspects one to four disclosed herein, the surfactant is present in an amount of 0 to 40 wt%, or 0 to 20 wt%, or 0.1 to 15 wt%, or 0.1 to 10 wt%, based on the total weight of the composition. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partly oxidized alk(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolysates (particularly wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates or amine oxides.
[0120] Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one COO(-) or SO3(-) group in the molecule. Particularly suitable zwitterionic surfactants are the so- called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example, cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N- dimethyl ammonium glycinates, for example, cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. The fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is an example that can be used.
[0121] Ampholytic surfactants are also suitable, particularly as co-surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C8 to C18 alkyl or acyl group, contain at least one free amino group and at least one — COOH or — SO3H group in the molecule and which are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, Nalkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N- alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N- cocoalkylaminopropionate, cocoacylami noethyl aminopropionate and acyl sarcosine.
[0122] Anionic surfactants are characterized by a water-solubilizing anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic group. Dermatologically safe anionic surfactants are known to the practitioner in large numbers from relevant textbooks and are commercially available. They are, in particular, alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts, alkylether sulfates, alkylether carboxylates, acyl isethionates, acyl sarcosinates, acyl taurines containing linear C12-C18 alkyl or acyl groups and sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.
[0123] Examples of suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more especially chlorides and bromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl ammonium chlorides and trialkyl methyl ammonium chlorides, for example, cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride. In addition, the readily biodegradable quaternary ester compounds, such as, for example, the dialkyl ammonium methosulfates and methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the name of Stepantexe and the corresponding products of the Dehyquart® series, may be used as cationic surfactants. “Esterquats” are generally understood to be quaternized fatty acid triethanolamine ester salts. They can provide the compositions with particular softness. They are known substances which are prepared by the relevant methods of organic chemistry. Other cationic surfactants suitable for use in accordance with the invention are the quaternized protein hydrolysates. EXPERIMENTAL SECTION Abbreviations
[0124] EHB is 2-ethylhexyl-3-hydroxybutyrate; g is gram; rpm is revolutions per minute; psig is pounds per square inch gauge; °C is degree(s) Celsius; h is hour(s); rt is room temperature; min is minute(s); pl is microliter(s); PP is polypropylene.
[0125] Example 1 : Synthesis of 2-ethylhexyl-3-hydroxybutyrate
[0126] 2-ethylhexyl acetoacetate (1350g) and catalyst (ES Cat 440 50% w / w basis, 38 g) were stirred (300 rpm) under a N2 atmosphere (1000psig) in a vessel, and then vessel with the reaction mixture was flushed with H2 (2x300psig) under continued agitation. The reaction mixture was then stirred under H2 (900 psig) at a temperature of 80°C for approximately 2 h. The reaction mixture was filtered, and the filtrate wad concentrate (in vacuo) to provide a crude product. The title compound was obtained after purification by distillation.
[0127] Example 2: Synthesis of n-octyl-3-hydroxybutyrate
[0128] Ex 2 can be prepared by adapting the synthetic procedure disclosed in WO 02 / 090312, Example 10.
[0129] Example 3: Synthesis of 2,3-dihydroxypropyl-2-ethylhexanoate
[0130] Ex 3 can be prepared by adapting the synthetic procedure disclosed in Zlatanos, S.N. et al., J. Am. Oil. Chem. Soc. (1985), 62(11), 1575-7.
[0131] Example 4: Synthesis of n-butyl-3-hydroxybutyrate
[0132] Ex 4 can be prepared by adapting the synthetic procedure disclosed in US20150038734. Sensory Triangle Test
[0133] Two commercial shampoos, Biotera (Henkel) and Better natured color care (Henkel), were used in the sensory triangle test. Mixtures were prepared according to Table 1 , water and EHB (Ex 1) samples were added to the shampoo using a Finnpipet micropipet (100-1 OOOpI). The mixture was homogenized using a magnetic stirrer (IKA) with stirring rod at maximum speed for minimal 30 min at rt.
[0134] Samples 1-4 (8 g) were randomized and subjected to the triangle discriminative test according to ASTM E 1885-18. The objective was to discriminate (perceivable difference) between formulations with and without the sensory enhancing component. The 12 untrained assessors were familiarized with the mechanics of the triangle test protocol. Each panelist was presented three samples for each type of shampoo. One of the three contained Ex 1 , while the other two did not contain Ex 1. Therefore, in a truly randomized study one would expect that the shampoo formulation containing Ex 1 would be identified 33% of the time. However, the panelists were able to identify the shampoo formulation containing Ex 1 50% of the time for both types of shampoos.
[0135] Table 1.
[0136] Panel test
[0137] Two commercial shampoos, The Ritual of Ayurveda (Rituals) and The Ritual of Jing (Rituals), were used in a sensory test. Mixtures were prepared according to Table 2, water and EHB (Ex 1) samples were added to the shampoo by gravimetrical means. The mixture was homogenized using a Speedmixer DAC 150.1 FVZ-K, at 1000 rpm for 5 min. Untrained assessors were asked to blindly evaluate the shampoo mixtures in pairs (Pair 1 : Sample 5 & 6 (n=8); Pair 2: Sample 7 & 8 (n=7)). The assessors were handed two blotters marked with a letter (for identification by the person giving the instructions), the shampoo sample was put onto the blotter with a Pasteur pipette. The order within the pairs was randomized, as well as the pairs. The panelists answered following questions:
[0138] 1 . Q1 : Which of both samples has the highest intensity?
[0139] 2. Q2: Do you notice a change in character between the two samples? Therefore, in a truly randomized study one would expect that the shampoo formulation containing Ex 1 would be identified 50% of the time. However, the panelists were able to identify the shampoo formulation containing Ex 1 more than 50% of the time for both types of shampoos, for both attributes.
[0140] Table 2.
Claims
CLAIMSWhat is claimed is:
1. A composition comprising:(i) a compound of formula I:wherein:G is -O(O)C- or -C(O)O-, wherein the hyphens represent the points of attachment;R1is an unbranched or branched (C4-12)alkyl ;R2is a hydrogen, an unbranched or branched (Ci-e)alkyl or an unbranched or branched (Ci-e)alkanol; and n is independently 1 , 2, or 3;(ii) at least one fragrance; and(iii) at least one of a non-aroma chemical carrier.
2. The composition of claim 1 , wherein G is -0(0)C-.
3. The composition of any one of claims 1-2, wherein R2is a (Ci-2)alkyl.
4. The composition of claim 3, wherein R2is methyl.
5. The composition of any one of claims 1-2, wherein R2is (Ci-2)alkanol.
6. The composition of any one of claims 1-2, or 5, wherein R2is -CH2-OH.
7. The composition of claim 1 , wherein G is -C(0)0-.
8. The composition of claim 7, wherein R2is a (Ci-2)alkyl.
9. The composition of claim 8, wherein R2is methyl.
10. The composition of claim 7, wherein R2is (Ci-2)alkanol.11 . The composition of claim 10, wherein R2is -CH2-OH.
12. The composition of any one of claims 1-11 , wherein R1is -CH2(CH2)2CH3,-CH(CH2CH3)(CH2)3CH3, -CH2CH(CH2CH3)(CH2)3CH3, or -CH2(CH2)6CH3.
13. The composition of any one of claims 1-12, wherein n is 1 .
14. The composition of claim 1 , wherein the compound of formula I is:(1) 2-ethylhexyl-3-hydrobutyrate 1 ,(2) n-octyl-3-hydroxybutyrate 2,(3) 2,3-dihydroxylpropyl-2-ethylhexanoate 3, or(4) n-butyl-3-hydroxybutyrate 4.
15. The composition of any one of claims 1-14, wherein the at least one nonaroma chemical carrier is a surfactant, an oil component, an antioxidant, a deodorant agent, a solvent, or combinations thereof.
16. The composition of any one of claims 1-15, wherein the composition is a perfume composition, a body care composition, a hygiene article, a cleaning composition, a textile detergent, a scent composition, a food, a food supplement, a pharmaceutical composition, or a crop protection composition.
17. The composition of any one of claims 1-16, wherein when the composition is subjected to the ASTM E1885-18 test, at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
18. A method of imparting an intense aroma impression to a composition comprising at least one fragrance, comprising adding a compound of formula I:wherein:G is -0(0)0 or -C(O)O-, wherein the hyphens represent the points of attachment;R1is an unbranched or branched (C4-12)alkylR2is a hydrogen, or an unbranched or branched (Ci -e)alkyl or an unbranched or branched (O-e)alkanol; and n is independently 1 , 2, or 3, to the composition, as determined according to the ASTM E1885-18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
19. Use of a compound of formula I:wherein:G is -O(O)C- or -0(0)0-, wherein the hyphens represent the points of attachment;R1is an unbranched or branched (C4-12)alkyl ;R2is a hydrogen, an unbranched or branched (Ci-e)alkyl or an unbranched or branched (Ci-6)alkanol; and n is independently 1 , 2, or 3, to impart an intense aroma impression to a composition comprising at least one fragrance, as determined according to the ASTM E1885- 18 test, wherein at least 50% of the panelists can detect an intense aroma impression relative to the composition modified without the compound of formula I.
20. The method or use of any one of claims 18-19, wherein G is -0(0)0-.21 . The method or use of any one of claims 18-20, wherein R2is a (Ci-2)alkyl.
22. The method or use of any one of claims 18-21 , wherein R2is methyl.
23. The method or use of any one of claims 18-22, wherein n is 1 .
24. The method or use of any one of claims 18-19, wherein G is -0(0)0-.
25. The method or use of any one of claims 18-19, or 24, wherein R2is (C1-2)alkanol.
26. The method or use of any one of claims 18-19, or 24-25, wherein R2is - CH2-OH.
27. The method or use of any one of claims 18-26, wherein n is 1 .
28. The method or use of any one of claims 18 or 19, wherein the compound of formula I is:(1) 2-ethylhexyl-3-hydrobutyrate 1 ,(2) n-octyl-3-hydroxybutyrate 2,(3) 2,3-dihydroxylpropyl-2-ethylhexanoate 3, or(4) n-butyl-3-hydroxybutyrate 4.
29. The method or use of any one of claims 18-28, wherein the composition is a perfume composition, a body care composition, a hygiene article, a cleaning composition, a textile detergent, a scent composition, a food, a food supplement, a pharmaceutical composition, or a crop protection composition.
Citation Information
Patent Citations
Method for producing an alkyl 3-hydroxybutyrate
US20150038734A1
Process for preparing carboxylic acids and derivatives thereof
WO2002090312A1
Topically applied two-phase cosmetic or dermatological composition, e.g. for skin or hair care or make-up removal, contains dimethylcarboxylic acid-alkanediol ester for rapid phase separation after use
FR2864893A1
α, α-disubstituted carboxylic acid esters for use as aroma chemicals
US11542221B2
Clear sunscreen gels and methods of use thereof
US20080206172A1