Stable Grapefruit Odor Compounds With Hydrolysis Resistance
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Solution Overview
Problem
There is a demand for novel odorants/compounds that provide grapefruit and related odor profiles, which are stable and suitable for use in fragrance, flavor, and deodorizing/masking compositions, as existing thiol-based and acetal/ester-based odorants are unstable due to hydrolysis and oxidation.
Innovation Solution
Development of odorous compounds denoted by formula (I), which are selected from specific stereoisomers and regioisomers, and include alkyl or alkylidene groups, with increased chemical stability, providing floral, grapefruit, citrus, and rhubarb odor profiles.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If thiol-based odorants are used to provide grapefruit odor profile, then the odor character is improved, but the stability deteriorates due to oxidation
Solution Approach 1:
The patent changes the chemical structure parameters by introducing specific functional groups (aldehyde, alcohol, ether) and molecular configurations (stereoisomers, regioisomers) to create compounds that maintain grapefruit odor profiles while exhibiting enhanced oxidative stability. The structural modifications include specific carbon chain lengths, double bond positions, and functional group arrangements that prevent oxidation while preserving aroma characteristics.
2Ease of manufacture
If acetal or ester-based odorants are used to provide grapefruit odor profile, then the odor character is improved, but the stability deteriorates due to hydrolysis
Solution Approach 1:
The patent modifies the chemical parameters by selecting specific functional groups (aldehyde, alcohol, ether) that are resistant to hydrolysis under acidic or basic conditions. The molecular structure parameters including carbon chain length, branching patterns, and functional group positioning are optimized to prevent hydrolytic degradation while maintaining the desired grapefruit odor character.
3Ease of manufacture
If natural fragrance ingredients are used to provide authentic odor profile, then the odor quality is improved, but the supply availability deteriorates due to increasing limitations
Solution Approach 1:
The patent creates synthetic compounds that replicate the odor profiles of natural fragrance ingredients through careful design of molecular structures. The synthetic compounds are designed to mimic the olfactory characteristics of natural grapefruit and citrus compounds while providing improved stability and availability, effectively copying the essential odor qualities without relying on limited natural supplies.
4Ease of manufacture
If existing odorants are used to provide fragrance, then the aroma is achieved, but the shelf life deteriorates due to instability
Solution Approach 1:
The patent optimizes multiple parameters including molecular weight, functional group composition, stereochemical configuration, and regioisomeric structure to create compounds that simultaneously provide desirable aroma characteristics and extended shelf life. The structural parameters are specifically adjusted to resist degradation pathways that would otherwise limit product longevity.
Data Source
AI summary
The present invention relates to compounds of formula (I), wherein A represents —CH2OH or —CHO, —CH2OAc R1 is an alkyl or alkylidene group, R2 is an alkyl or alkylidene group, dotted line represents double bond or single bond. The present invention also relates to a method of preparation of the compounds and a composition comprising the compounds which is used in perfumed, flavored, deodorizing, masking composition.