2-oxaspiro[5.5]undecene derivatives for stable grapefruit odorants
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Solution Overview
Problem
Conventional odorants with grapefruit and cassis characteristics, such as sulphur-containing compounds, are unstable and costly, while non-sulphur-containing compounds often produce unpleasant off-odors, leading to a need for new compounds that enhance or modify odour notes effectively.
Innovation Solution
The use of substituted 1-alkoxy-2-oxaspiro[5.5]undec-8-enes, which can exist as mixtures of stereoisomers, are employed as fragrance or flavor compounds, offering improved stability and odor profiles without the drawbacks of prior art compounds, and can be combined with base materials or used in various fragrance applications.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If sulphur-containing compounds are used to achieve grapefruit and cassis odor characteristics, then the desired odor profile is obtained, but the compounds become unstable and may cause unpleasant off-odors
Solution Approach 1:
The patent changes the chemical parameters of the odorant molecules by replacing sulphur-containing functional groups with oxygen-containing functional groups (specifically 1-alkoxy substituents on the 2-oxaspiro[5.5]undec-8-ene core structure). This parameter change maintains the desired grapefruit and cassis odor characteristics while eliminating the instability and off-odor problems associated with sulphur compounds.
Solution Approach 2:
The patent employs a simpler, more stable molecular structure (non-sulphur 2-oxaspiro[5.5]undec-8-ene derivatives) that replaces the problematic sulphur-containing compounds. This substitution provides a more reliable and stable odorant that does not suffer from the degradation and off-odor issues of sulphur compounds, effectively making the new compounds a superior long-term solution.
2Reliability
If non-sulphur-containing compounds are used to avoid instability and off-odors, then compound stability is improved, but the compounds become expensive
Solution Approach 1:
The patent describes a versatile synthetic route using 2-oxaspiro[5.5]undec-8-ene as a core structure that can produce multiple different odorant compounds by varying only the substituent groups (R1, R2, R3, R4). This multi-functionality allows a single synthetic platform to generate various stable, non-sulphur odorants with different odor profiles, reducing overall development and manufacturing costs compared to creating separate synthesis routes for each compound.
Solution Approach 2:
The patent modifies molecular parameters (substituent types and positions) on a stable core structure to achieve different odor characteristics without compromising stability. This systematic parameter variation allows for cost-effective production of multiple odorant variants from a single robust synthetic platform, avoiding the need for expensive, complex synthesis routes for each individual compound.
3Measurement precision
If stereoisomers are resolved to obtain isomerically pure forms, then odor profile precision is improved, but manufacturing complexity and purification difficulty increase
Solution Approach 1:
The patent acknowledges that while isomerically pure forms provide superior odor profiles, the additional complexity and cost of resolution may not always be justified. The invention provides the option to use racemic mixtures when the application does not require the highest level of odor precision, allowing manufacturers to apply partial action (using mixtures) when sufficient and reserve full action (resolution) for applications requiring maximum precision.
Data Source
AI summary
Disclosed are substituted 2-oxaspiro[5.5]undec-8-ene derivatives of formula (I) and their use as odorants. This disclosure relates furthermore to a method of their production and flavor and fragrance compositions comprising them.