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CN-122028893-A - Composition and method for producing the same

CN122028893ACN 122028893 ACN122028893 ACN 122028893ACN-122028893-A

Abstract

Provided herein are compositions comprising a) a powerful 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 perfumed product to provide a cooling sensation on the skin.

Inventors

  • N. Kohito Amanino

Assignees

  • 奇华顿股份有限公司

Dates

Publication Date
20260512
Application Date
20241003
Priority Date
20231012

Claims (15)

  1. 1. A composition comprising A) A strong-effect cool compound which contains a main component, B) And a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof.
  2. 2. A composition according to claim 1 wherein the powerful cooling compound is selected from the group consisting of 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one and N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide.
  3. 3. The composition of claim 1, wherein the powerful cooling compound is present 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.
  4. 4. A composition according to any preceding claim, wherein the weight ratio of the powerful cooling compound (a) to solvent (b) is from 1:3 to 1:99.
  5. 5. A composition according to any preceding claim comprising, consisting essentially of, or consisting of, relative to the weight of the total composition, (a) 1 to 25 wt% of the powerful cooling compound according to formula (I), and (b) 75 to 99 wt% of the solvent selected from 2-phenylethanol, phenoxyethanol, and mixtures thereof, provided that (a) and (b) add up to 100 wt%.
  6. 6. Use of a composition according to any preceding claim in a fragrance formulation.
  7. 7. A fragrance formulation comprising a composition as defined in any one of claims 1 to 4, further comprising at least one fragrance compound.
  8. 8. A fragrance formulation according to claim 6, further comprising an additional cooling compound selected from the group consisting of 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -acetamide, 2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) ethyl) cyclohexane-1-carboxamide (including (1 r,2s,5 r) -2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) ethyl) cyclohexane-1-carboxamide), N- (4- (cyanomethyl) phenyl) -2-isopropyl-5-methylcyclohexane-carboxamide (including (1 r,2s,5 r) -N- (4- (cyanomethyl) phenyl) -2-isopropyl-5-methylcyclohexane-carboxamide), N-ethyl-p-menthane-3-carboxamide, (2-isopropyl-5-methylcyclohexane-1-carbonyl) glycine ethyl ester, 2-isopropyl-N, 2, 3-trimethylbutanamide, N- (4- (2-amino-2-oxoethyl) phenyl) -2-isopropyl-5-methylcyclohexane-1-carboxamide (including rac- (1R, 2S, 5R) -N- (4- (2-amino-2-oxoethyl) phenyl) -2-isopropyl-5-methylcyclohexane-1-carboxamide), 2-isopropyl-5-methylcyclohexyl 2-hydroxypropionate, N- (2-hydroxy-2-phenylethyl) -2-isopropyl-5, 5-dimethylcyclohexane-1-carboxamide.
  9. 9. A perfumed product comprising a product base and a composition according to any of claims 1 to 5 or a perfume formulation according to claim 7 or 8.
  10. 10. A perfumed product according to claim 9, comprising the composition in a proportion that provides a cooling effect.
  11. 11. A method of incorporating a powerful cooling compound into a perfumed product, comprising: a) Mixing said potent cooling compound or salt or solvate thereof with a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof, and B) The resulting composition is added to the perfumed product.
  12. 12. A method according to claim 11 wherein the powerful cooling compound is selected from the group consisting of 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one and N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide.
  13. 13. A method of providing a perfumed product with a cooling sensation for the skin, comprising adding to the product base a composition according to any of claims 1 to 5 in a ratio that provides a cooling effect.
  14. A crystalline form of 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one characterized by its main peaks in its powder X-ray diffraction pattern at the following 2Θ angles of 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, obtained using copper ka radiation.
  15. 15. A process for preparing a solution of the crystalline form of 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one according to claim 14, comprising the step of dissolving the crystalline form of 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one in a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof.

Description

Composition and method for producing the same Technical Field The present invention relates to compositions, especially compositions for use in perfumery, comprising a specific cooling compound and a solvent, and to the use of said compositions in perfumery and perfumery products. Furthermore, it relates to a perfumed product comprising said composition. Background Compounds that provide a cooling sensation play an important role in the flavour and fragrance industry to create associations with freshness and cleanliness. Cooling compounds are widely used in a variety of products, such as foods, tobacco products, beverages, dentifrices, mouthwashes, toothpastes, and toiletries. The cooling sensation contributes to the appeal and acceptability of the consumer product. Patent application WO2021074281A1 discloses a new class of chemical compounds capable of activating TRPM8 (transient receptor potential melastatin member 8, also known as Trp-p8 or MCR 1) ion channels, inducing cold sensation. One embodiment in said application is 2-methyl-1- (2- (5- (p-tolyl) -1H-imidazol-2-yl) piperidin-1-yl) butan-1-one. It is a very powerful cooling compound at low concentrations, but it exists in solid form at room temperature, making it challenging to handle. Incorporation of solids into consumer products, which may be in liquid or pasty form, is not always easy. In addition, the powdered ingredients must be handled carefully to avoid dust hazards associated therewith. Thus, there remains a need to provide cooling compounds in a form that is convenient and safe to use in further formulation operations and that remains stable over prolonged storage in that form. SUMMARY According to a first aspect of the present invention there is provided a composition comprising: a) A strong-effect cool compound which contains a main component, B) And a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof. According to a second aspect of the present invention there is provided the use of the composition in a fragrance formulation. According to a third aspect of the present invention there is provided a fragrance formulation comprising the composition. According to a fourth aspect of the present invention there is provided a perfumed product comprising the composition. According to a fourth aspect of the present invention there is provided a method of incorporating a powerful cooling compound into a perfumed product. According to a fifth aspect of the present invention there is provided a method of providing a perfumed product with a cooling sensation for the skin. According to a sixth aspect of the present invention there is provided a method of preparing a solution of a cooling compound comprising the step of dissolving a crystalline, powerful cooling compound in a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof. Certain embodiments of any aspect of the invention may provide one or more of the following advantages: The strong cooling compound is easier to handle; avoiding discoloration; A stable solution; specific olfactory contribution of solvent, and A perfumed product providing an additional cooling sensation. The details, examples, and preferred embodiments provided with respect to any specific one or more of the described aspects of the invention will be further described herein and equally apply to all aspects of the invention. Unless otherwise indicated herein or unless clearly contradicted by context, any combination of embodiments, examples and preferences described herein are encompassed by the present invention, in all possible variations thereof. Detailed description of the preferred embodiments The present invention is based on the surprising finding that a powerful cooling compound in solid form at ambient temperature can be provided in the form of a composition in a specific solvent to allow incorporation into a perfumed product. Thus, a first embodiment of the present invention provides a composition comprising: a) A strong-effect cool compound which contains a main component, B) And a solvent selected from the group consisting of 2-phenylethanol, phenoxyethanol and mixtures thereof. Such compositions can be easily incorporated into perfumed products without the drawbacks of handling solids. The composition may improve and/or enhance the fresh clean feel of the perfumed product and/or increase the olfactive impression of the perfumed product. It may help provide a cooling sensation for the skin through the perfumed product into which it is incorporated, while the solvent additionally contributes to the overall fragrance of the product. 2-Phenylethanol (phenylethanol, CAS No. 60-12-8) and phenoxyethanol (2-phenoxyethan-1-ol, CAS No. 122-99-6) are not typical solvents for use in perfuming compositions, but they allow to dissolve the powerful cooling compounds in relatively high amounts, for example in amounts of at least 10% by