Powdery Musky Macrocycles with Controlled E/Z Isomer Ratios
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Solution Overview
Problem
Existing perfumery ingredients, such as Habanolide®, lack the ability to enhance the nitro-musk aspect while maintaining the ambrette facet, and the exact organoleptic properties of individual isomers are unknown, limiting the perfumer's palette.
Innovation Solution
A novel composition comprising specific ratios of (Z)-oxacyclohexadec-12-en-2-one, (E)-oxacyclohexadec-12-en-2-one, and (Z)-oxacyclohexadec-13-en-2-one isomers, with a weight ratio of E-diastereoisomers to Z-diastereoisomers between 40:60 and 15:85, providing a powerful musky/powdery note with an amber aspect.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If existing macrocyclic musk compounds (e.g., Habanolide®) are used, then musk notes are provided, but the nitro-musk aspect cannot be enhanced while maintaining the ambrette facet
Solution Approach 1:
The invention segments the macrocyclic musk compound into its individual diastereoisomeric components (E and Z isomers at positions 12 and 13), allowing independent analysis and control of each isomer's contribution to the overall olfactive profile. This segmentation enables the perfumer to understand and manipulate specific isomeric ratios to achieve desired scent characteristics.
Solution Approach 2:
The invention changes the critical parameter of isomeric composition by providing a specific method to enrich Z-isomers and control the E:Z ratio within defined ranges (40:60 to 15:85). This parameter control allows optimization of the nitro-musk aspect while preserving the ambrette facet, resolving the contradiction between enhancing one aspect and maintaining another.
2Manufacturing precision
If synthesis methods producing mainly E isomers are used, then high purity E-isomer products are obtained, but Z isomer enrichment is not achieved
Solution Approach 1:
Instead of attempting to produce Z-isomers directly from synthesis (which yields mainly E-isomers), the invention inverts the approach by starting with the readily obtain E-isomer-rich products and applying specific enrichment methods to increase the Z-isomer content. This inversion leverages existing synthesis capabilities while achieving the desired isomeric distribution.
Solution Approach 2:
The invention changes the isomeric composition parameter through controlled enrichment processes that selectively increase Z-isomer content. By adjusting the enrichment degree, the final E:Z ratio can be precisely controlled within the 40:60 to 15:85 range, achieving both high manufacturing precision and versatile isomeric distribution control.
3Ease of manufacture
If the exact organoleptic properties of individual isomers are unknown, then synthesis can proceed without isomer separation, but the perfumer's palette remains limited
Solution Approach 1:
The invention performs preliminary characterization of individual isomer properties before final product formulation. By identifying and documenting the organoleptic properties of each diastereoisomer in advance, the perfumer gains knowledge that enables precise formulation design, expanding the available perfumery palette while maintaining manufacturing efficiency.
Solution Approach 2:
The invention introduces isomeric composition control as an intermediary between simple synthesis and complex perfumery application. By establishing standardized isomeric ratios (E:Z from 40:60 to 15:85) as intermediate products, the invention bridges the gap between easy synthesis and versatile perfumery applications, allowing perfumers to select and combine isomers based on known properties.
Data Source
AI summary
Described herein is a composition of matter includinga) 0.5 to 85% w/w of (Z)-oxacyclohexadec-12-en-2-one;b) 0.5 to 30% w/w of (E)-oxacyclohexadec-12-en-2-one;c) 0 to 30% w/w of (E)-oxacyclohexadec-13-en-2-one; andd) 0.5 to 85% w/w of (Z)-oxacyclohexadec-13-en-2-one,the percentage being relative to the total weight of the composition of matter;wherein the weight ratio of the E-diastereoisomers to the Z-diastereoisomers is in the range between 40:60 and 15:85.