Partially Saturated Cyclohexene Compounds for Muguet Fragrance
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Solution Overview
Problem
There is a need for novel fragrance ingredients that can impart a muguet odour characteristic, as compounds like Lyral ™ have allergenic concerns and regulatory limitations, and existing replacers do not provide powerful, long-lasting, clean, and diffusive notes.
Innovation Solution
Development of partially saturated organic compounds with specific carbon-carbon bond configurations and stereoisomers, such as 3-(4-(2-hydroxy-2-methylpropyl)cyclohex-1-en-1-yl)propanal, which offer a powerful and long-lasting lily-of-the-valley odour with clean and very diffusive notes, suitable for both consumer and fine fragrances.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Power
If aromatic derivatives are used to provide muguet odour, then odour strength is improved, but odour transparency and natural effect deteriorate
Solution Approach 1:
The patent changes the chemical structure parameter from aromatic ring to partially saturated cyclohexene ring, which fundamentally alters the molecular geometry from flat to bent. This structural parameter change achieves both strong odour (comparable to aromatic analogues) and transparent, natural odour characteristics that aromatic compounds lack.
2Power
If Lyral is used as fragrance ingredient, then muguet odour characteristic is improved, but safety and regulatory compliance worsen due to allergenic concerns
Solution Approach 1:
The patent creates novel compounds that copy the desirable muguet odour characteristics of Lyral without using the allergenic structure. The partially saturated cyclohexene compounds replicate the olfactory profile (powerful, long-lasting, clean, diffusive notes) while having fundamentally different chemical structures that avoid allergenicity.
3Object-affected harmful factors
If existing replacer compounds are used, then regulatory compliance is improved, but odour performance deteriorates as they lack powerful and long-lasting notes
Solution Approach 1:
The patent optimizes the molecular structure parameters of cyclohexene derivatives, specifically the positioning of hydroxy and methyl groups, and the saturation level of the ring. These parameter changes result in compounds with low odour thresholds and long-lasting, powerful muguet notes, significantly improving upon existing replacers.
4Object-affected harmful factors
If fully saturated analogues are used, then safety is improved, but odour strength deteriorates with higher odour threshold value
Solution Approach 1:
Instead of full saturation (which would eliminate odour strength), the patent uses partial saturation with one or two carbon-carbon double bonds in the cyclohexene ring. This partial unsaturation maintains the bent molecular structure for safety while preserving sufficient odour strength, achieving a balance between safety and performance.
Data Source
AI summary
A compound according to formula I in the form of any one of its stereoisomers or a mixture thereof (l) wherein is indicating a carbon-carbon single or double bond, with the provision that the compound has one carbon-carbon double bond or two isolated or conjugated carbon-carbon double bonds, and R1 to R5 are independently from each other selected from H or Me, with the proviso that the compound is not 3-(4-(2-hydroxy-2-methylpropyl)cyclohex-1-en-1-yl)propanal, and its use as fragrance.