Oxygenated Terpenoids for Long-Lasting Woody Fragrance
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Solution Overview
Problem
The correlation between the structure and odor of terpenoids is not fully understood, making it difficult to predict which compounds will possess desirable odor properties, particularly in perfumery where woody, ambery, and musky notes are crucial, and existing compounds lack substantial longevity on surfaces.
Innovation Solution
The development of oxygen-containing tri- and tetra-cyclic terpenoids with specific structural features, such as varying distances between the oxygen atom and the lipophilic center, which are used in fragrance compositions to provide powerful, long-lasting woody, ambery, and musky odor notes, and can be used alone or in combination with other odorant molecules.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Duration of action of moving object
If the oxygen atom is linked directly or via C1-spacer group to the cyclic ring system in known terpenoids, then the molecular structure is simpler and easier to manufacture, but the odor longevity (substantivity) on surfaces is insufficient
Solution Approach 1:
The patent changes the key parameter of the spacer group length between the oxygen atom and the cyclic ring system. By increasing the spacer length from C1 or direct linkage to C2-C5 spacer groups, the odor longevity is significantly improved while maintaining reasonable molecular complexity for manufacturing
Solution Approach 2:
The patent creates composite molecular structures by combining the oxygen-containing functional group with specific terpenoid ring systems through extended spacer chains, achieving enhanced odor persistence while maintaining the characteristic woody, ambery, and musky odor profiles
2Manufacturing precision
If stereoisomers are resolved to prepare individual forms, then the odor purity and specificity is improved, but the manufacturing complexity and purification difficulty increases
Solution Approach 1:
The patent applies partial resolution strategies where complete stereoisomer separation is not always required. By achieving sufficient enantiomeric excess through selective crystallization or chiral chromatography, the desired odor specificity is obtained without the excessive complexity of complete isomer separation
Solution Approach 2:
The patent uses chiral pool synthesis where naturally occurring chiral building blocks are utilized, allowing the production of enantiomerically enriched compounds without requiring complex resolution steps, thus simplifying manufacturing while maintaining odor purity
Data Source
AI summary
The use as fragrance ingredient of a compound of formula (I) wherein R1 and Y have the same meaning as given in the description, and fragrance applications comprising them.