Substituted 2-oxa-bicyclooctane Fragrance Compounds
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Solution Overview
Problem
The fragrance industry faces a need for new chemical entities that can create unique and varied fragrances, as small differences in chemical structures significantly impact odor and characteristics, limiting the creation of new perfumes and personal care products.
Innovation Solution
The development of novel substituted 2-oxa-bicyclo[2.2.2]octane derivative compounds, which are used as fragrance materials in perfumes, colognes, personal products, and fabric care products, providing distinct fragrance notes such as woody, cedar-like, animalic, and fresh characteristics.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If new chemical entities are developed to create unique fragrances, then the variety and uniqueness of fragrance profiles is improved, but the complexity of chemical structure development and synthesis is increased
Solution Approach 1:
The patent applies segmentation by developing a series of compounds based on a core 2-oxa-bicyclo[2.2.2]octane framework with systematically varied substituents. Each compound differs by specific molecular modifications (different R1-R5 groups), allowing perfumers to create varied fragrance profiles from a structured family of related molecules rather than entirely new chemical structures.
Solution Approach 2:
The patent utilizes parameter changes by modifying specific molecular parameters (substituent types, positions, and configurations) within the 2-oxa-bicyclo[2.2.2]octane core structure. By changing parameters such as alkyl chain lengths, aromatic group types, and stereochemical configurations, the invention generates diverse fragrance characteristics from a single molecular scaffold.
2Adaptability or versatility
If small differences in chemical structures are utilized to create new fragrances, then the creativity and uniqueness of perfume formulations is improved, but the difficulty of predicting and controlling odor characteristics is increased
Solution Approach 1:
The patent applies copying by creating multiple compounds that replicate and vary upon a successful core structure. The 2-oxa-bicyclo[2.2.2]octane framework serves as a template that has been successfully validated for fragrance application, and numerous derivatives are generated by copying this successful design with modified substituents, reducing the risk of developing entirely new molecular architectures.
Solution Approach 2:
The patent implements local quality by making targeted modifications at specific positions (R1-R5) within the molecular structure while maintaining the integrity of the core framework. This allows precise control over which parts of the molecule are modified to achieve desired odor characteristics, rather than fundamentally changing the entire molecular architecture.
3Quantity of substance
If novel compounds are synthesized and tested for fragrance applications, then the availability of new fragrance materials is improved, but the time and resources required for synthesis and evaluation are increased
Solution Approach 1:
The patent applies universality by designing a multi-functional compound family where the same core structure (2-oxa-bicyclo[2.2.2]octane) can generate multiple fragrance materials with different characteristics by simply changing substituents. This single universal scaffold can produce numerous fragrance variants for different product applications (perfumes, colognes, personal care products) without requiring separate synthesis routes for each compound.
Solution Approach 2:
The patent implements preliminary action by establishing the core 2-oxa-bicyclo[2.2.2]octane framework and its synthesis methodology before developing the full range of substituted derivatives. This preliminary development of the core structure and its basic properties allows for efficient subsequent modification and derivation of multiple fragrance compounds from a solid foundation rather than starting from scratch for each variant.
Data Source
AI summary
The present invention is directed to novel fragrance compounds and their unexpected advantageous use in improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of the compounds, wherein the compounds are represented by the following formula:wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen and C1-C5 alkyl.