Optically Active Musk Ketone for Fragrance Odor Quality

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Solution Overview

Problem

Current compounds with a cyclopentane ring, such as 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)pentanol, have unpleasant or very weak odors and lack stereoisomer evaluation, failing to provide a highly regarded scent.

Innovation Solution

Development of optically active 1'R isomers of 3-methyl-5-(2,2,3-trimethylcyclopentan-1-yl)-2-pentanone with specific optical purity ranges, which exhibit a pleasant strong musk odor and good diffusibility, used in fragrance compositions for cosmetics and other products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If racemic compounds with cyclopentane rings are used, then the structure is simple and easy to manufacture, but the odor is unpleasant or very weak

Engineering Contradiction:
Improveease of manufactureVSAvoidodor quality
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by transitioning from racemic mixtures to optically active isomers. Specifically, it identifies that the (1'R)-isomer of 3-methyl-5-(2,2,3-trimethylcyclopentan-1-yl)-2-pentanone exhibits a pleasant strong musk odor, while the racemic form has unpleasant or very weak odor. This resolves the contradiction by changing the stereochemical parameter while maintaining the same molecular structure, thus improving odor quality without complicating the manufacturing process.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If optically active isomers are used, then the odor quality is improved, but the manufacturing process becomes more complex

Engineering Contradiction:
Improveodor qualityVSAvoiddevice complexity
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent employs preliminary action by using chiral pool synthesis or asymmetric synthesis methods to produce optically active isomers directly from the beginning, rather than attempting to resolve racemic mixtures later. This approach obtains the desired (1'R)-isomer with high optical purity through pre-planned chiral synthesis routes, thereby improving odor quality while minimizing the complexity of the overall manufacturing process.

Inventive Principle:
Principle #10Preliminary action

3Object-affected harmful factors

If high optical purity is achieved, then the musk odor and diffusibility are enhanced, but the production cost increases

Engineering Contradiction:
ImprovediffusibilityVSAvoidproduction cost
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent utilizes the principle of copying by identifying and replicating the specific stereochemical configuration ((1'R)-isomer) that naturally exhibits the desired strong musk odor and good diffusibility. By copying this successful natural configuration through asymmetric synthesis or chiral pool methods, the patent achieves high optical purity and enhanced sensory properties without requiring excessively complex or costly production processes.

Inventive Principle:
Principle #26Copying

Data Source

PatentEP3042891B1Fragrance composition
Publication Date: 2018.08.15 TAKASAGO INTERNATIONAL CORP
  • EP3042891B1 patent drawing
  • EP3042891B1 patent drawing
  • EP3042891B1 patent drawing

AI summary

The present invention provides a compound represented by the following general formula (A): wherein 1'-position is optically active; and one of R1 and R2 represents a methyl group and the other represents an ethyl group, or both R1 and R2 represent a methyl group.