Composition

Abstract

Provided herein are compositions comprising a) a potent cooling compound b) and a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol, and mixtures thereof. The composition may be incorporated into a perfuming product to provide a cool feel on the skin.

Description

Technical Field

[0001] This invention relates to compositions, particularly compositions for use in fragrance formulations, comprising specific cooling compounds and solvents, and to the use of said compositions in fragrance formulations and flavored products. Furthermore, it relates to flavored products comprising said compositions.

[0002] background

[0003] Compounds that provide a cooling sensation play a vital role in the fragrance and flavor industry, generating associations with freshness and cleanliness. Cooling compounds are widely used in a variety of products, such as food, tobacco products, beverages, dental floss, mouthwash, toothpaste, and toiletries. The cooling sensation helps enhance the appeal and acceptability of consumer products.

[0004] Patent application WO2021074281A1 discloses a new class of chemical compounds that can activate the TRPM8 (transient acceptor potential melastatin member 8, also known as Trp-p8 or MCR1) ion channel, inducing a cooling sensation. One embodiment of the application is 2-methyl-1-(2-(5-(p-tolyl)-1 H (-Imidazol-2-yl)piperidin-1-yl)but-1-one. It is a very potent cooling compound at low concentrations, but it exists as a solid at room temperature, making it challenging to handle. Incorporating a solid into a consumer product, which may be in liquid or paste form, is not always easy. Furthermore, powdered ingredients must be handled with care to avoid the dust hazards associated with them.

[0005] Therefore, there is still a need to provide cooling compounds in the form that are convenient and safe for use in further formulation operations and remain stable after long-term storage.

[0006] Overview

[0007] According to a first aspect of the invention, a composition is provided comprising:

[0008] a) A potent cooling compound,

[0009] b) and a solvent, wherein the solvent is selected from 2-phenylethanol, phenoxyethanol and mixtures thereof.

[0010] According to a second aspect of the invention, the use of the composition in flavoring formulations is provided.

[0011] According to a third aspect of the invention, a fragrance formulation comprising the composition is provided.

[0012] According to a fourth aspect of the invention, a flavored product comprising the composition is provided.

[0013] According to a fourth aspect of the present invention, a method for incorporating a potent cooling compound into a flavored product is provided.

[0014] According to a fifth aspect of the invention, a method is provided for providing a cooling sensation to the skin in a fragranced product.

[0015] According to a sixth aspect of the invention, a method for preparing a solution of a cooling compound is provided, comprising the step of dissolving a crystalline potent cooling compound in a solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof.

[0016] Certain embodiments of any aspect of the present invention may provide one or more of the following advantages:

[0017] Easier to handle potent cooling compounds;

[0018] To avoid discoloration;

[0019] Stable solution;

[0020] The special olfactory contribution of solvents; and

[0021] Fragranced products that provide an extra cooling sensation.

[0022] Any specific details, examples, and preferred embodiments provided with respect to any aspect of the invention will be further described herein and will also apply to all aspects of the invention. Unless otherwise stated herein, or unless obviously contradicted by the context, any combination of the embodiments, examples, and preferred embodiments described herein, with all possible variations, is covered by the invention.

[0023] Detailed Explanation

[0024] This invention is based on the surprising discovery that potent cooling compounds, which exist in solid form at room temperature, can be provided as compositions in specific solvents to allow incorporation into flavored products.

[0025] Therefore, a first embodiment of the present invention provides a composition comprising:

[0026] a) A potent cooling compound,

[0027] b) and a solvent, wherein the solvent is selected from 2-phenylethanol, phenoxyethanol and mixtures thereof.

[0028] This composition can be easily incorporated into fragranced products without the drawbacks of handling solids. The composition can improve and / or enhance the fresh, clean feel of the fragranced product, and / or increase the olfactory impression of the fragranced product. It can help provide a cooling sensation on the skin through the fragranced product into which it is incorporated, while the solvent additionally contributes to the overall fragrance of the product.

[0029] 2-Phenylacetylethanol (phenylethanol, CAS No. 60-12-8) and phenoxyethanol (2-phenoxyethyl-1-ol, CAS No. 122-99-6) are not typical solvents for use in fragrance compositions, but they allow for the dissolution of the potent cooling compound in relatively high amounts, such as at least 10% by weight or more, for example at at least 20% by weight or more, or even at more than 25% by weight.

[0030] The compositions of the potent cooling compounds according to the invention in solvents are only pale yellow, which is acceptable in many applications. Furthermore, the compositions are stable during storage, showing no precipitation for at least two months at 21°C.

[0031] The solvent has a slight but noticeable floral odor, which is not always necessary for all applications. However, the odor is very versatile and blends well with different odor profiles, such as floral, balsam, oriental, mossy, herbal, or "modern aldehyde" compositions. It is easy to use in a wide range of different applications. In certain embodiments, it can help provide compressed fragrance, minimizing the volume of odorless solvent required in the composition.

[0032] For example, the potent cooling compound is selected from 2-methyl-1-(2-(5-(p-tolyl)-1 H -imidazol-2-yl)piperidin-1-yl)but-1-one and N -(1 H -pyrazole-3-yl)- N -(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide.

[0033] Both cooling compounds are solids, therefore the composition of such compounds according to the invention allows for easier handling.

[0034] 2-Methyl-1-(2-(5-(p-Tolyl)-1 H (-Imidazol-2-yl)piperidin-1-yl)but-1-one has two stereocenters and exists in the form of different enantiomers, diastereomers, tautomers, or mixtures thereof. The compositions of the present invention may comprise a mixture of isomers of the potent cooling compound. Alternatively, a single isomer or a group of diastereomers may be used, for example (2... R)-2-methyl-1-(2-(5-(p-tolyl)-1 H -imidazol-2-yl)piperidin-1-yl)but-1-one.

[0035] For example, the compositions according to the invention comprise (a) 2-methyl-1-(2-(5-(p-tolyl)-1 H (b) 2-Imidazol-2-yl)piperidin-1-yl)but-1-one and (b) 2-phenylethanol.

[0036] For example, the potent cooling compound is present in at least 1% or more by weight of the total composition, or at least 5% or more by weight of the total composition, or at least 10% or more by weight of the total composition, or at least 15% or more by weight of the total composition, or at least 20% or more by weight of the total composition, or at least 25% or more by weight of the total composition.

[0037] For example, the weight ratio of the potent cooling compound (a) to the solvent (b) is 1:3 to 1:99.

[0038] For example, 2-methyl-1-(2-(5-(p-tolyl)-1 H The weight ratio of 1-imidazol-2-yl)piperidin-1-yl)but-1-one to 2-phenylethanol is 1:3 to 1:99. For example, it is 1:4, or 1:10, or 1:25, or 1:50, or 1:75, or 1:80, or 1:90, or 1:95.

[0039] For example, 2-methyl-1-(2-(5-(p-tolyl)-1 H The weight ratio of 1-imidazol-2-yl)piperidin-1-yl)but-1-one to phenoxyethanol is 1:3 to 1:99. For example, it is 1:4, or 1:10, or 1:25, or 1:50, or 1:75, or 1:80, or 1:90, or 1:95.

[0040] For example, N -(1 H -pyrazole-3-yl)- N The weight ratio of 1-(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide to 2-phenylethanol is 1:3 to 1:99. For example, it is 1:4, or 1:10, or 1:25, or 1:50, or 1:75, or 1:80, or 1:90, or 1:95.

[0041] For example, the composition comprises, is substantially composed of, or consists of: (a) 1-25% by weight of a potent cooling compound according to formula (I) relative to the total composition, and (b) 75-99% by weight of a solvent selected from 2-phenylethanol, phenoxyethanol and mixtures thereof, provided that (a) and (b) together reach 100 by weight.

[0042] Many other typical solvents used in fragrances are unsuitable for this potent cooling compound. Poor solubility (e.g., 2-methyl-1-(2-(5-(p-tolyl)-1-) H (-Imidazol-2-yl)piperidin-1-yl)but-1-one in DPG, triethyl citrate and isopropyl myristate (less than 5%), solutions exhibit strong color development (e.g. in lactic acid), solutions are unstable (e.g. in benzyl benzoate, butanediol), or the solvent is not used at all in fragrance applications.

[0043] In further embodiments of the invention, the use of the above-described composition in fragrance formulations is provided. The composition can be readily mixed with other ingredients, such as those comprising at least one fragrance compound and / or additional cooling compounds, and / or a product matrix, to provide an olfactory impression and a cooling effect.

[0044] In another embodiment of the invention, a fragrance formulation is provided comprising the above-described composition, and further comprising at least one fragrance compound. The composition may be used as is, but in other instances, the composition comprises at least one or more fragrance compounds.

[0045] For example, the at least one or more fragrance compounds are selected from methyl dihydrojasmonate (CAS: 24851-98-7), linalool (CAS: 78-70-6), ambroxol (CAS: 54464-57-2), cis-3-hexenol, dihydromyrcenol (CAS: 18479-58-8), benzyl acetate, citronellol (CAS: 106-22-9), tricyclic terpene aldehyde (CAS: 68039-49-6), peach aldehyde (CAS: 104-67-6), linalyl acetate, styraxyl acetate (CAS: 93-92-5), coumarin (CAS: 91-64-5), o-tert-butylcyclohexyl acetate (CAS: 20298-69-5), and galena (CAS: 20298-69-5). 1222-05-5), ethyl vanillin (CAS: 121-32-4), cis-3-hexenyl acetate, ethylene brassinolate (CAS: 105-95-3), hexylcinnamaldehyde (CAS: 101-86-0), vanillin (CAS: 121-33-5), ambroxan (CAS: 6790-58-5), β-ionone (CAS: 79-77-6), and β-decyl lactone (CAS: 706-14-9).

[0046] Additional fragrance compounds that may be present in fragrance formulations together with the compositions according to the invention are described, for example, in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 2003, and include fragrance compounds and essential oils of natural or synthetic origin.

[0047] In another embodiment of the invention, a fragrance formulation is provided comprising the above-described composition, and further comprising an additional cooling compound. The additional cooling compound may enhance or alter the cooling effect provided and the olfactory impression provided.

[0048] For example, the other cooling compound may be selected from: 2-(4-ethylphenoxy)- N -(1 H -pyrazole-3-yl)- N -(thiophene-2-ylmethyl)acetamide, 2-isopropyl-5-methyl- N -(2-(pyridin-2-yl)ethyl)cyclohexane-1-carboxamide (including (1 R ,2 S 5 R )-2-Isopropyl-5-methyl- N-(2-(pyridin-2-yl)ethyl)cyclohexane-1-carboxamide), N -(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexaneformamide (including (1) R ,2 S 5 R )- N -(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexane-formamide), N- Ethyl-p-menthane-3-carboxamide, (2-isopropyl-5-methylcyclohexane-1-carbonyl)glycine ethyl ester, 2-isopropyl- N 2,3-Trimethylbutyramide, N -(4-(2-amino-2-oxoethyl)phenyl)-2-isopropyl-5-methylcyclohexane-1-carboxamide (including rac-(1 R ,2 S 5 R )- N -(4-(2-amino-2-oxoethyl)phenyl)-2-isopropyl-5-methylcyclohexane-1-carboxamide), 2-isopropyl-5-methylcyclohexyl 2-hydroxypropionic acid, N -(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, menthol (e.g., in the form of peppermint oil and / or spearmint oil), menthone, menthyl lactate, menthone glycerol acetal, 3-(1-menthoxy)-propane-1,2-diol, p-menthane-3,8-diol, isoprene, menthyl succinate monomenthate, o-menthylglycerol, menthyl N , N -Dimethylsuccinamide, 2-(sec-butyl)cyclohexane-1-one, 3-(benzo[d][1,3]dioxacyclopentadien-5-yl)- N , N -Diphenylacrylamide, 4-(2-(4-allyl-2,6-dimethoxyphenoxy)-1-ethoxypropyl)-2-methoxyphenol, 4-(2-(4-allyl-2,6-dimethoxyphenoxy)-1-((2-isopropyl-5-methylcyclohexyl)oxy)propyl)-2-methoxyphenol (including 4-(2-(4-allyl-2,6-dimethoxyphenoxy)-1-(((1 S ,2 R 5 S )-2-isopropyl-5-methylcyclohexyl)oxy)propyl)-2-methoxyphenol) and 4-(2-(4-allyl-2,6-dimethoxyphenoxy)-1-(((1 R ,2 S 5 R)-2-isopropyl-5-methylcyclohexyl)oxy)propyl)-2-methoxyphenol), N -(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide N -(4-(cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexaneformamide and N -(3-hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexaneformamide.

[0049] In another embodiment of the invention, a flavored product is provided, comprising a product base and the above-described composition or the above-described fragrance preparation.

[0050] For example, the fragrance product may be selected from fabric care and personal care products.

[0051] Typical examples of fabric care products include acidic, alkaline, or neutral detergents, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatments, fabric softeners, laundry sheets, laundry soaps, and others. For example, fabric care products designed for use in high-temperature countries or regions.

[0052] Typical examples of personal care products are body care products, hair care products, or cosmetic products, especially creams and lotions, soaps, body gels, shower gels, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products such as shampoos and conditioners (liquid or solid form), dry shampoos, hair sprays, deodorants, antiperspirants, and decorative cosmetic products.

[0053] For example, the scented product contains the above-described composition in proportions that provide a cooling effect. A cooling effect can be achieved if the scented product is applied directly to the skin. Alternatively, a cooling effect can be achieved if a fabric treated with the scented product comes into contact with the skin.

[0054] For example, the flavored product contains at least 10 ppm of the potent cooling compound, such as 20 ppm, 50 ppm, 100 ppm, or more. Assuming the composition of the present invention has 25% by weight of the potent cooling compound, the flavored product contains at least 40 ppm of the composition, such as 80 ppm, 200 ppm, 400 ppm, or more. Assuming the composition of the present invention has 10% by weight of the potent cooling compound, the flavored product contains at least 100 ppm of the composition, such as 200 ppm, 500 ppm, 1000 ppm, or more.

[0055] In another embodiment of the invention, a method for incorporating a potent cooling compound into a flavored product is provided, comprising:

[0056] a) Mix the potent cooling compound or its salt or solvate with a solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof, and

[0057] b) Add the resulting composition to the flavored product.

[0058] For example, a method is provided in which the potent cooling compound is selected from 2-methyl-1-(2-(5-(p-tolyl)-1 H -imidazol-2-yl)piperidin-1-yl)but-1-one and N -(1 H -pyrazole-3-yl)- N -(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide.

[0059] For example, a method of providing a cooling sensation on the skin to a scented product includes adding the above-described composition in a proportion that provides the cooling effect to the product base. For example, the cooling effect can be provided by at least 10 ppm, such as 20 ppm, 50 ppm, 100 ppm, or more of the potent cooling compound in the scented product. The proportion of the composition in the scented product can be determined depending on the concentration of the composition (up to 25% by weight), for example, 0.004% or more of the composition in the scented product.

[0060] As used in this article, “product matrix” means a composition used as a consumer product to perform a specific action (such as cleaning, softening, and care).

[0061] Due to the high potency of the cooling compounds and the challenges of handling solid materials, these cooling compounds should be provided as solutions, particularly in solvents suitable for flavored consumer products. Known, for example, as the potent cooling compound 2-methyl-1-(2-(5-(p-tolyl)-1 H (-Imidazol-2-yl)piperidin-1-yl)but-1-one can form different polymorphs (three-dimensional crystal structures), which may have different physical properties, such as solubility, due to their unique three-dimensional crystal structures.

[0062] 2-methyl-1-(2-(5-(p-tolyl)-1-) can be obtained H (-Imidazol-2-yl)piperidin-1-yl)but-1-one, in a crystalline form having the structure described in Example 3. This polymorph has low solubility in the most common solvents used in fragranced consumer products, likely due to the high stability of its crystalline form. Therefore, it is necessary to dissolve the potent cooling compound to provide it as a solution.

[0063] Typically, it is impossible to predict whether a particular organic compound will form different crystal forms, and what structures and properties each crystal form might possess. It has been found that 2-methyl-1-(2-(5-(p-tolyl)-1-) has been obtained by recrystallization. H The most stable polymorph of (-imidazol-2-yl)piperidin-1-yl)but-1-one. It is characterized by a main peak at the following 2θ angles in its powder X-ray diffraction pattern obtained using copper K-α radiation: 9.53, 11.61, 12.90, 14.28, 14.51, 17.10, 19.15, 19.41, 19.56, 19.88, 20.70, 21.03, 22.61, 27.07, and 28.81 degrees. The polymorph requires a specific solvent, such as 2-phenylethanol, phenoxyethanol, or mixtures thereof, for dissolution.

[0064] In one embodiment of the present invention, a potent cooling compound, 2-methyl-1-(2-(5-(p-tolyl)-1 ... H A polymorph of (-imidazol-2-yl)piperidin-1-yl)but-1-one is characterized by a main peak as shown in Example 3 in its powder X-ray diffraction pattern obtained using copper K-α radiation. A solution of the polymorph in 2-phenylethanol, phenoxyethanol, or a mixture thereof is also provided. A method for preparing a solution of a cooling compound is also provided, comprising the step of dissolving a crystalline, potent cooling compound in a solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof.

[0065] The invention will now be further described with reference to the following non-limiting embodiments. These examples are for illustrative purposes only, and it should be understood that variations and modifications can be made by those skilled in the art.

[0066] Example

[0067] Example 1: Determination of solubility

[0068] The concentrations (wt%) of the potent cooling compound in the selected solvents used for solubility determination were 50%, 40%, 30%, 25%, 20%, 15%, 10%, 5%, 2.5%, and 1%. The solubility of the potent cooling compound was determined by placing 100 mg of the compound in a vial and adding an appropriate amount of solvent to achieve the concentration corresponding to the solubility to be determined (e.g., 300 mg of solvent for a solubility of 25 wt%). The mixture was then heated to 50°C for 1 hour to aid dissolution, and then allowed to stand at room temperature (21°C) for 16 hours. After this period, the mixture was visually inspected to determine whether the solution was clear or whether any precipitate had formed. The vial was then refrigerated at 4°C for 20 hours, then brought back to 21°C and maintained at that temperature for 16 hours before re-examining the solubility. The mixture was then kept at 21°C for 2 months to monitor for any long-term precipitation or discoloration. The table below shows the maximum observed concentration maintained in solution at 21°C even after the above refrigeration cycles.

[0069]

[0070] Example 2: Application in Fragrance-Enhanced Consumer Products

[0071] According to Example 1, 20 wt% of 2-methyl-1-(2-(5-(p-tolyl)-1-methyl ... H A solution of (-imidazol-2-yl)piperidin-1-yl)but-1-one was named "Potential Cooling Compound Solution". This solution was then incorporated into a fragrance formulation according to the following formula.

[0072]

[0073]

[0074] The resulting fragrance formulation is incorporated into soap bar applications according to the following procedure:

[0075] I purchased "Palmosalt N 3021" (noodle-like) soap base with the following specifications from KLK OLEO (Malaysia):

[0076] Ingredients: Sodium palmitate, sodium palm kernel oleate, water, glycerin, sodium chloride, hydroxyethyl diphosphate, sodium hydroxide.

[0077] Total fat content: 79-82%

[0078] Moisture: 10-13%

[0079] Free alkali, calculated as NaOH: 0.01-0.05%

[0080] Glycerin: 0.2-0.4%

[0081] Preservatives: present

[0082] 99g of the soap base was placed in a stainless steel beaker and combined with 1g of the fragrance formulation containing a potent cooling compound solution prepared above. The mixture was stirred with a large metal spatula until the fragrance formulation was completely absorbed by the soap base. The mixture was then fed into the funnel of a soap extruder, pushed with a plastic pestle, and the formulation was recovered in the beaker. The resulting material was fed back into the extruder and the process was repeated three times to obtain a satisfactory distribution of the fragrance formulation in the matrix and a uniform appearance of the soap bar. The final soap bar was cut into four pieces, each weighing approximately 25g.

[0083] Alternatively, the potent cooling compound solution can be added directly to the application, for example, along with the remaining flavorings, without pre-mixing the two.

[0084] Three team members then used the resulting soap bars to wash their hands and forearms, comparing them to soap prepared using the same procedure but omitting the potent cooling compound solution in the fragrance formulation (by replacing it with 2-phenylethanol). During use, both soaps exhibited a pleasant, refreshing, floral, rose-like, and aldehyde fragrance. It was found that the soap containing the potent cooling compound solution produced a highly perceptible and lasting cooling sensation on the skin for up to 15 minutes after use, without burning or stinging. In contrast, the soap bar without the potent cooling compound solution did not induce any cooling effect.

[0085] Example 3: 2-Methyl-1-(2-(5-(p-Tolyl)-1 H Crystallization of 1-imidazol-2-yl)piperidin-1-yl)but-1-one and determination of polymorphism by powder XRD (X-ray diffraction).

[0086] The obtained 2-methyl-1-(2-(5-(p-tolyl)-1- H A sample of (e.g., as described in WO2021074281A1) imidazol-2-yl)piperidin-1-yl)but-1-one was recrystallized: it was dissolved in hot ethyl acetate (or a similar ester solvent) and then cooled to obtain the desired polymorphic material in white needle-like form. The obtained powder was analyzed by powder XRD (using copper K-α radiation) and by... Figure 1 The spectral characterization in the image exhibits the following characteristic peaks:

[0087] .

Claims

1. A composition comprising a) A potent cooling compound, b) and a solvent, wherein the solvent is selected from 2-phenylethanol, phenoxyethanol and mixtures thereof.

2. The composition according to claim 1, wherein the potent cooling compound is selected from 2-methyl-1-(2-(5-(p-tolyl)-1 ... H -imidazol-2-yl)piperidin-1-yl)but-1-one and N -(1 H -pyrazole-3-yl)- N -(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide.

3. The composition of claim 1, wherein the potent cooling compound is present in at least 1% or more, or at least 5% or more, or at least 10% or more, or at least 15% or more, or at least 20% or more, or at least 25% or more, by weight of the total composition.

4. The composition according to any one of the preceding claims, wherein the weight ratio of the potent cooling compound (a) to the solvent (b) is 1:3 to 1:

99.

5. The composition according to any one of the preceding claims, comprising, substantially consisting of, or consisting of the following: The total composition comprises, relative to the weight of (a) 1-25% by weight of the potent cooling compound according to formula (I) and (b) 75-99% by weight of the solvent selected from 2-phenylethanol, phenoxyethanol and mixtures thereof, provided that (a) and (b) together reach 100% by weight.

6. Use of the composition according to any one of the preceding claims in a fragrance formulation.

7. A flavoring preparation comprising the composition defined in any one of claims 1 to 4, further comprising at least one flavoring compound.

8. The flavoring formulation according to claim 6, further comprising a additional cooling compound selected from 2-(4-ethylphenoxy)- N -(1H-pyrazole-3-yl)- N -(thiophene-2-ylmethyl)acetamide, 2-isopropyl-5-methyl- N -(2-(pyridin-2-yl)ethyl)cyclohexane-1-carboxamide (including (1 R ,2 S 5 R )-2-Isopropyl-5-methyl- N -(2-(pyridin-2-yl)ethyl)cyclohexane-1-carboxamide), N -(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexane-formamide (including (1) R ,2 S 5 R )- N -(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexane-formamide), N ethyl-p-menthane-3-carboxamide, (2-isopropyl-5-methylcyclohexane-1-carbonyl)glycine ethyl ester, 2-isopropyl- N 2,3-Trimethylbutyramide, N -(4-(2-amino-2-oxoethyl)phenyl)-2-isopropyl-5-methylcyclohexane-1-carboxamide (including rac-(1 R ,2 S 5 R )- N -(4-(2-amino-2-oxoethyl)phenyl)-2-isopropyl-5-methylcyclohexane-1-carboxamide), 2-isopropyl-5-methylcyclohexyl 2-hydroxypropionic acid, N -(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide.

9. A flavored product comprising a product base and a composition according to any one of claims 1 to 5 or a flavoring preparation according to claim 7 or 8.

10. The flavored product of claim 9, wherein the composition comprises a proportion that provides a cooling effect.

11. A method for incorporating a potent cooling compound into a flavored product, comprising: a) Mix the potent cooling compound or its salt or solvate with a solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof, and b) Add the resulting composition to the flavored product.

12. The method according to claim 11, wherein the potent cooling compound is selected from 2-methyl-1-(2-(5-(p-tolyl)-1 ...(2-(5-(p-tolyl)-1-(2-(5-(p-tolyl)-1-(2-(5-(p-toly H -imidazol-2-yl)piperidin-1-yl)but-1-one and N -(1 H -pyrazole-3-yl)- N -(thiophene-2-ylmethyl)-2-(p-tolyloxy)acetamide.

13. A method for providing a cooling sensation to the skin in a scented product, comprising adding to a product base a proportion of the composition according to any one of claims 1 to 5 that provides the cooling effect. 14,2-Methyl-1-(2-(5-(p-Tolyl)-1 H The crystal form of 1-imidazol-2-yl)piperidin-1-yl)but-1-one, characterized by The main peak in its powder X-ray diffraction pattern obtained using copper Kα radiation is located at the following 2θ angle: 9.53, 11.61, 12.90, 14.28, 14.51, 17.10, 19.15, 19.41, 19.56, 19.88, 20.70, 21.03, 22.61, 27.07 and 28.81 degrees.

15. Preparation of the 2-methyl-1-(2-(5-(p-tolyl)-1-methyl)-1-methyl as described in claim 14 H A method for preparing a solution of the crystalline form of 2-methyl-1-(2-(5-(p-tolyl)-1-yl)but-1-one, comprising preparing a solution of the crystalline form of the 2-methyl-1-(2-(5-(p-tolyl)-1-yl)but-1-one. H The step of dissolving the crystalline form of 2-imidazol-2-yl)piperidin-1-yl)but-1-one in a solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof.

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