Aryl-Substituted Alkanal Perfume Ingredients for Lilial Replacement
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Solution Overview
Problem
The use of Lilial ™, an aryl-substituted alkanal, is under regulatory scrutiny due to its toxic effects on reproductive organs, necessitating a replacement with perfume ingredients that exhibit similar muguet odour characteristics without CMR-related issues.
Innovation Solution
Aryl-substituted alkanal perfume ingredients with a substituent ortho to the aldehyde functionality and/or butanal as the aldehyde functionality are used, providing similar odour characteristics to Lilial ™ but with reduced enzymatic degradation to benzoic acid derivatives.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If Lilial™ is used as a perfume ingredient, then muguet odour characteristics are achieved, but toxic effects on reproductive organs occur leading to regulatory restrictions
Solution Approach 1:
The patent creates structural analogs of Lilial™ by modifying the molecular structure (changing the alkyl group from tert-butyl to isobutyl, and adding ortho-methyl substitution) to copy the desirable muguet odour characteristics while eliminating the harmful metabolic pathway that produces toxic benzoic acid derivatives
Solution Approach 2:
The patent changes specific molecular parameters of the perfume ingredient: substituting the tert-butyl group with isobutyl group, and adding a methyl group at the ortho position. These parameter changes alter the metabolic fate of the compound, preventing formation of toxic metabolites while preserving the muguet odour profile
2Ease of operation
If Lilial™ is used to achieve muguet odour, then desirable fragrance characteristics are obtained, but enzymatic degradation to benzoic acid derivatives occurs causing regulatory issues
Solution Approach 1:
The patent converts the harmful metabolic pathway into a beneficial outcome by designing a molecule where the isobutyl side chain undergoes oxidative degradation to produce isobutyric acid instead of benzoic acid, and the ortho-methyl group metabolizes to sulfur dioxide. This metabolic redirection eliminates toxic effects while maintaining fragrance performance
Solution Approach 2:
By changing the chemical structure parameters (isobutyl instead of tert-butyl, ortho-methyl substitution), the patent fundamentally alters the enzymatic degradation pathway to produce non-toxic metabolic products, thereby eliminating regulatory concerns while preserving the desired odour characteristics
Data Source
AI summary
The use of a compound represented by the formula I wherein R1 through R4 is independently H or methyl; and R6 is a branched or linear, saturated or unsaturated C3-C7 alkyl, alkenyl, cycloalkyl or cycloalkenyl residue, as perfume ingredients in personal care and household care products.