All-Syn Crotonates for Safe Perfumery Fragrance
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Solution Overview
Problem
Fragrance compounds like Damascone Alpha, Beta, and Delta are skin sensitizers, restricting their use due to potential skin irritation, and crotonic acid esters with fruity notes have off-odors that hinder commercialization, despite offering desirable fruity and floral impressions.
Innovation Solution
Development of 5- or 6-membered cycloalkyl or cycloalkenyl crotonates with an all-syn configuration, which are less skin sensitizing and stable against enzymatic hydrolysis, reducing off-odor formation, allowing for their use in perfumery with enhanced safety and efficacy.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If Damascone compounds are used to provide fruity and floral fragrance notes, then the desired fragrance quality is achieved, but skin sensitization occurs leading to usage restrictions
Solution Approach 1:
The patent changes the chemical structure parameters of the fragrance compound by replacing the Damascone core structure with a crotonate ester structure (changing functional groups and molecular configuration). This structural parameter change maintains the desirable fruity-floral olfactory properties while eliminating the skin sensitization activity, allowing safe use in perfumery applications.
Solution Approach 2:
The invention creates a new compound (crotonate ester) that copies or mimics the key sensory property (fruity-floral odor) of the Damascone compounds without copying their harmful biological activity (skin sensitization). The crotonate ester serves as a safe alternative that replicates the desired fragrance characteristic while avoiding the adverse effects.
2Reliability
If crotonic acid esters with fruity notes are used to provide fresh and floral impressions, then desirable fragrance notes are achieved, but off-odors are produced that hinder commercialization
Solution Approach 1:
The patent optimizes the structural parameters of the crotonic acid esters by specifically selecting the cyclohexyl or cyclohexenyl ring structure with particular substitution patterns. This structural refinement changes the odor profile parameters to eliminate off-odors while preserving the desirable fresh fruity-floral notes, making the compounds suitable for commercial perfumery use.
3Reliability
If conventional crotonic acid esters are used to provide fruity fragrance notes, then fresh and floral impressions are achieved, but enzymatic hydrolysis occurs leading to off-odor formation
Solution Approach 1:
The patent modifies the molecular structure parameters of the crotonic acid esters by incorporating the cyclohexyl or cyclohexenyl ring system with specific substitution patterns. This structural change increases resistance to enzymatic hydrolysis, preventing the breakdown that leads to off-odor formation, while maintaining the desirable fresh fruity-floral fragrance characteristics.
Data Source
AI summary
A compound of formula Iwherein R1, R2, R3 and R4 can be independently selected from H or Me,n=0, 1,the dotted lines are indicating single bonds, or in case n=0 an isolated double bond at position 3′, or in case n=1 an isolated double bond at position 3′ or 4′,and the wavy bond is indicating an unspecified configuration of the adjacent double bond. Said compounds, as well as precursors capable to generate said compounds, are useful as fragrance ingredients.