Search

EP-4737544-A1 - PERFUME COMPOSITION

EP4737544A1EP 4737544 A1EP4737544 A1EP 4737544A1EP-4737544-A1

Abstract

Provided is a fragrance composition containing the following 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) as an active ingredient. The fragrance composition contains 3-(4-alkylphenyl)propanenitrile having a floral scent, and a green scent or a fruity scent, as an active ingredient and has a strong floral scent. Further, use of 3-(4-alkylphenyl)propanenitrile as a fragrance, a scenting method, and a method for producing 3-(4-alkylphenyl)propanenitrile are provided. In Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.

Inventors

  • UTAMURA, Tatsuya
  • NISHIUCHI, JUNYA

Assignees

  • MITSUBISHI GAS CHEMICAL COMPANY, INC.

Dates

Publication Date
20260506
Application Date
20240617

Claims (17)

  1. A fragrance composition, comprising 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) as an active ingredient: where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.
  2. The fragrance composition according to claim 1, further comprising a fragrance substance other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1).
  3. The fragrance composition according to claim 2, wherein the fragrance substance other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) comprises at least one selected from the group consisting of hydrocarbons, alcohols, esters, phenols, aldehydes, ketones, acetals, ketals, ethers, natural essential oils, natural extracts, and nitriles other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1).
  4. The fragrance composition according to any one of claims 1 to 3, wherein R is at least one selected from the group consisting of an ethyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.
  5. The fragrance composition according to any one of claims 1 to 4, wherein R is at least one selected from the group consisting of an isopropyl group, an n-butyl group, and an isobutyl group.
  6. The fragrance composition according to any one of claims 1 to 5, wherein R is an n-butyl group.
  7. The fragrance composition according to any one of claims 1 to 6, wherein 3-(2-alkylphenyl)propanenitrile represented by General Formula (2) is contained in an amount of from 0.03 to 0.8 mass% based on the 3-(4-alkylphenyl)propanenitrile represented by Formula (1): where in Formula (2), R represents an alkyl group having from 2 to 4 carbon atoms.
  8. Use of 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) as a fragrance: where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.
  9. The use according to claim 8, wherein R is at least one selected from the group consisting of an ethyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.
  10. The use according to claim 8 or 9, wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, and a green scent or a fruity scent.
  11. The use according to any one of claims 8 to 10, wherein R is at least one selected from the group consisting of an isopropyl group and an isobutyl group.
  12. The use according to claim 11, wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, a green scent, and a fruity scent.
  13. The use according to any one of claims 8 to 10, wherein R is an n-butyl group.
  14. The use according to claim 13, wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, a fruity scent, and a spicy scent.
  15. A scenting method, comprising imparting a floral scent, and a green scent or a fruity scent, with 3-(4-alkylphenyl)propanenitrile represented by General Formula (1): where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.
  16. A method for producing 3-(4-alkylphenyl)propanenitrile, the method comprising, in this order: a step of converting, via a condensation reaction, 4-alkylbenzaldehyde represented by Formula (3) as a raw material and acetonitrile into cinnamonitrile represented by Formula (4); and a hydrogenation step: where in Formulae (3) and (4), R represents an alkyl group having from 2 to 4 carbon atoms.
  17. A nitrile composition, comprising 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) and 3-(2-alkylphenyl)propanenitrile represented by General Formula (2), wherein the 3-(2-alkylphenyl)propanenitrile represented by General Formula (2) is contained in an amount of from 0.03 to 0.8 mass% based on the 3-(4-alkylphenyl)propanenitrile represented by Formula (1): where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms, and, in Formula (2), R represents an alkyl group having from 2 to 4 carbon atoms.

Description

Technical Field The present invention relates to a fragrance composition. Background Art As nitrile compounds having a phenyl group, there are known, as fragrance components, Peonile (2-cyclohexylidene-2-phenylacetonitrile) having a grapefruit, geranium, rose floral-like aroma, cinnamyl nitrile having a cinnamon, cassia-like aroma, and the like (Non-Patent Literature 1). It is known that some nitriles corresponding to aldehydes used as fragrances have similar aromatic notes. Non-Patent Literature 2 describes a method for deriving a corresponding nitrile from aldehydes used as a fragrance, and that the derived nitrile is useful as a fragrance component. Citation List Non-Patent Literature Non-Patent Literature 1: "Zoho Shin pan, Gousei Koryo: Kagaku to Shohin Chisiki (Enlarged and Revised Edition, Synthetic Fragrance: Chemistry and Product Knowledge)" edited by the Synthetic Fragrance Editing Committee, The Chemical Daily Co. Ltd., 2016, pages 725 to 726Non-Patent Literature 2: Flavor Fragrance Journal, 2020, vol. 35, pp. 425 to 435 Summary of Invention Technical Problem As described above, although some nitrile compounds have been used as fragrances, a novel scent is required to increase value of products, such as fragrance products, cosmetic products, detergents, sanitary products, general goods, medical and pharmaceutical products, and food products. Typically, a fragrance is used as a blended fragrance obtained by mixing a plurality of fragrances, and a fragrance component exhibiting an excellent effect especially when mixed with another fragrance is demanded. An object of the present invention is to provide a fragrance composition having novel scent and characteristics, use of a compound that can impart novel scent and characteristics to the fragrance composition, and a scenting method. Solution to Problem The present inventors have found that a fragrance composition contains a specific nitrile compound as an active ingredient and therefore has novel scent and characteristics, that the nitrile compound can be used as a fragrance, and that the nitrile compound can impart a scent useful as a fragrance, and thus completed the present invention. That is, the present invention is as follows. [1] A fragrance composition, containing 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) as an active ingredient: where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.[2] The fragrance composition according to [1], further containing a fragrance substance other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1).[3] The fragrance composition according to [2], wherein the fragrance substance other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) contains at least one selected from the group consisting of hydrocarbons, alcohols, esters, phenols, aldehydes, ketones, acetals, ketals, ethers, natural essential oils, natural extracts, and nitriles other than the 3-(4-alkylphenyl)propanenitrile represented by Formula (1).[4] The fragrance composition according to any one of [1] to [3], wherein R is at least one selected from the group consisting of an ethyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.[5] The fragrance composition according to any one of [1] to [4], wherein R is at least one selected from the group consisting of an isopropyl group, an n-butyl group, and an isobutyl group.[6] The fragrance composition according to any one of [1] to [5], wherein R is an n-butyl group.[7] The fragrance composition according to any one of [1] to [6], wherein 3-(2-alkylphenyl)propanenitrile represented by General Formula (2) is contained in an amount of from 0.03 to 0.8 mass% based on the 3-(4-alkylphenyl)propanenitrile represented by Formula (1): where in Formula (2), R represents an alkyl group having from 2 to 4 carbon atoms.[8] Use of 3-(4-alkylphenyl)propanenitrile represented by General Formula (1) as a fragrance: where in Formula (1), R represents an alkyl group having from 2 to 4 carbon atoms.[9] The use according to [8], wherein R is at least one selected from the group consisting of an ethyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.[10] The use according to [8] or [9], wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, and a green scent or a fruity scent.[11] The use according to any one of [8] to [10], wherein R is at least one selected from the group consisting of an isopropyl group and an isobutyl group.[12] The use according to [11], wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, a green scent, and a fruity scent.[13] The use according to any one of [8] to [10], wherein R is an n-butyl group.[14] The use according to [13], wherein the 3-(4-alkylphenyl)propanenitrile represented by Formula (1) imparts a floral scent, a fruity scent, and a spicy scent.[15] A sc