Campholenic Aldehyde Derivatives for Diverse Odor Profiles

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Solution Overview

Problem

The fragrance industry faces a constant demand for new compounds that can enhance, modify, or improve odor notes, with existing compounds lacking the desired range of odour characteristics.

Innovation Solution

Development of a novel class of campholitic aldehyde derivatives, specifically compounds of formula (I), which exhibit valuable odour characteristics ranging from floral, green, fruity to spicy and patchouli, woody notes, and can be used alone or in combination with known fragrances.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing fragrance compounds are used, then the current odor notes are maintained, but the demand for new and improved odor characteristics cannot be met

Engineering Contradiction:
Improveodor characteristics rangeVSAvoidcompound structure complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of campholenic aldehyde through variations in substitution patterns (R1-R6 groups), oxidation states (aldehyde, alcohol, ketone), and saturation levels. This creates a series of derivatives with progressively modified odor profiles, allowing the fragrance industry to achieve diverse odor characteristics from a standardized core structure rather than developing entirely new complex molecules.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention segments the fragrance compound into a core campholenic aldehyde structure with variable substituent groups (R1-R6). This segmentation allows independent optimization of different molecular regions - the core provides the characteristic camphoraceous notes while the substituents fine-tune specific odor attributes, enabling systematic development of new fragrance profiles without overwhelming structural complexity.

Inventive Principle:
Principle #1Segmentation

2Manufacturing precision

If stereoisomers are resolved to prepare individual stereoisomers, then the purity and specificity of the fragrance note is improved, but the complexity of manufacture and purification increases

Engineering Contradiction:
Improvestereoisomer purityVSAvoidpurification process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent employs preliminary action by using chiral starting materials (enantiomerically pure or enriched terpenoids) in the synthesis process. This ensures that the desired stereochemistry is established early in the synthesis pathway, allowing subsequent steps to proceed without complex resolution processes. The chiral information is built into the molecule from the beginning rather than requiring separation later.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention utilizes natural chiral templates from terpenoid chemistry as copying models. By starting with naturally occurring chiral compounds like campholenic aldehyde and performing transformations that preserve or selectively modify stereochemistry, the process replicates the efficient chiral synthesis found in nature, avoiding the need for complex artificial resolution systems.

Inventive Principle:
Principle #26Copying

Data Source

PatentEP2252674B1Organic compounds
Publication Date: 2011.09.07 GIVAUDAN SA
  • EP2252674B1 patent drawing
  • EP2252674B1 patent drawing
  • EP2252674B1 patent drawing

AI summary

The present invention refers to the use as flavour or fragrance of a compound of formula (I) wherein R4 is hydrogen and the bond between C-3 and C-4 is a single bond or the dotted line together with the bond between C-3 and C-4 represents a double bond; or R4 is methylene, forming with C-3 and C-4 a cyclopropane ring; R3 is hydrogen, C1, C2, C3, C4, C5, C6 alkyl, or C2, C3, C4, C5, C6 alkenyl; and I) R1 and R2 together with the carbon atom to which they are attached form a carbonyl group; or II) R1 is hydroxyl and R2 is selected from C1, C2, C3 alkyl, and C2, C3, C4 alkenyl.