Methyl-Substituted Macrocyclic Lactones for Musky Fragrance Profiles
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Solution Overview
Problem
There is a need for new, unique musk odorants that can effectively blend with floral heart notes in perfumes, providing a warm, sweet-herbaceous, aromatic character and are diffusive and powerful, while being economically viable and naturally authentic, as existing macrocyclic musks are limited and costly.
Innovation Solution
Development of methyl-substituted double-unsaturated macrocyclic lactones with specific ring configurations and chiral centers, allowing for the creation of compounds like (4E,9Z)-13-methyloxacyclopentadeca-4,9-dien-2-one, which offer intense, pleasant sweet aromatic-powdery musk odors with floral facets, and can be used as racemic mixtures for economic reasons, blending well with floral notes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If new methyl-substituted double-unsaturated macrocyclic lactones are developed to provide unique musk odorants with floral side notes, then the fragrance profile and diffusion are improved, but the manufacturing complexity increases due to chiral centers and specific stereochemical requirements
Solution Approach 1:
The patent applies parameter changes by systematically varying the ring size (14-17 atoms), substitution patterns (methyl group positions), and double bond configurations (E/Z isomers) to create a series of macrocyclic lactone compounds with optimized fragrance properties. This allows tuning of the musk odor characteristics while managing manufacturing complexity through structured molecular design
Solution Approach 2:
Instead of resolving individual enantiomers through complex chiral separation processes, the patent inverts the approach by utilizing racemic mixtures that directly exhibit the desired fragrance properties. This reversal of the conventional chiral resolution strategy significantly simplifies manufacturing while maintaining the unique floral-musk character of the compounds
2Ease of manufacture
If racemic mixtures are used instead of resolving stereoisomers, then the manufacturing cost is reduced, but the manufacturing precision and optical purity are compromised
Solution Approach 1:
The patent employs racemic mixtures as a cost-effective alternative to expensive enantiomerically pure compounds. By accepting the reduced optical purity of racemic mixtures, the manufacturing process becomes economically viable while still achieving the desired fragrance effects, effectively treating the optical impurity as an acceptable trade-off for significant cost reduction
Solution Approach 2:
The invention changes the purity parameter from requiring enantiomerically pure materials to accepting racemic compositions. This parameter change in optical purity specification enables the use of simpler, more economical manufacturing routes while maintaining sufficient fragrance performance through the characteristic musk-herbaceous profile of the macrocyclic lactones
Data Source
AI summary
The present invention refers to methyl-substituted double-unsaturated macrocyclic lactones comprising 14 to 17 ring atoms of formula (I) wherein n and m are independently selected from 1, 2, 3 and 4 with the proviso that 3 = n + m = 6. The invention relates furthermore to their use as odorant and fragrance composition comprising them.