Cyclohexenyl Methanol Esters for Multi-Faceted Odor Profiles

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Solution Overview

Problem

The fragrance industry lacks fragrance compounds with improved organoleptic properties, and there is a need for new chemical structures that can enhance or modify the odor characteristics of existing fragrance compositions.

Innovation Solution

The development of fragrance compounds, such as cyclohex-3-en-1-ylmethyl 2-hydroxypropanoate, cyclohex-3-en-1-ylmethyl 3-oxobutanoate, and their stereoisomers, which can be used alone or incorporated into fragrance compositions to provide multi-faceted odors and enhance the odor properties of consumer products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If new fragrance compounds are developed to improve organoleptic properties, then odor characteristics are enhanced, but research and development time and resources increase

Engineering Contradiction:
Improveorganoleptic propertiesVSAvoiddevelopment time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent applies parameter changes by systematically varying the R group in Formula I (different hydroxy-containing groups such as CH(OH)CH3, CH2(CO)CH3, and CH2OH) to create multiple fragrance compounds with improved organoleptic properties. This approach allows for efficient exploration of chemical space and identification of optimal fragrance molecules without extensive de novo synthesis.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If new chemical structures are created to provide unique odor characteristics, then fragrance versatility is improved, but synthesis complexity increases

Engineering Contradiction:
Improvefragrance versatilityVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent employs segmentation by dividing the fragrance compound into distinct functional segments: the cyclohex-3-en-1-ylmethyl core structure and the variable R group containing hydroxy functionality. This modular approach allows independent optimization of each segment and simplifies synthesis by enabling separate preparation and subsequent coupling of fragments.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates composite fragrance molecules by combining the cyclohex-3-en-1-ylmethyl scaffold with various hydroxy-containing groups (R = CH(OH)CH3, CH2(CO)CH3, or CH2OH). This composite structure integrates different functional properties within a single molecule, achieving versatile odor characteristics while maintaining reasonable synthesis complexity.

Inventive Principle:
Principle #40Composite materials

Data Source

PatentEP3468526B1Fragrance material
Publication Date: 2021.05.12 TAKASAGO INTERNATIONAL CORP
  • EP3468526B1 patent drawing
  • EP3468526B1 patent drawing
  • EP3468526B1 patent drawing

AI summary

Fragrance compounds having a unique chemical structure are provided, including esters and ethers of 3-cyclohexenyl methanol and derivatives thereof. The fragrance compounds can have multi-faceted odors. The fragrance compounds can be used alone or incorporated into a fragrance composition and/or consumer product to modify or enhance the odor of the fragrance composition and/or consumer product.