Alkanenitrile Odorants With Stable Woody and Patchouli Notes

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Solution Overview

Problem

Existing fragrance compounds lack unique odour profiles and stability, limiting their effectiveness in perfumery and fragrance applications.

Innovation Solution

Development of 3-(2-methylenealkoxy)alkanenitrile derivatives with diverse odour notes such as dry, woody, dusty, and patchouli, which are synthesized through advantageous stepwise operations, enhancing stability and compatibility with other fragrance materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing fragrance compounds are used, then fragrance compositions can be created, but the odour profiles lack uniqueness and stability is limited

Engineering Contradiction:
ImprovestabilityVSAvoidodour profile diversity
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of nitrile compounds - specifically using 3-(2-methylenealkoxy)alkanenitrile derivatives with varying alkyl chain lengths and substitutions. This structural parameter modification results in compounds with enhanced stability while maintaining diverse odour profiles including dry, woody, dusty, and patchouli notes, thereby resolving the contradiction between stability and odour profile diversity

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If novel 3-(2-methylenealkoxy)alkanenitrile derivatives are synthesized, then unique odour profiles and superior stability are achieved, but synthesis complexity increases

Engineering Contradiction:
Improveodour profile uniquenessVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The synthesis is divided into segmented steps: first preparing the nitrile compound, then reacting it with 2-methylenealdehyde in a second step. This segmentation of the synthesis process makes the complex reaction sequence more manageable and controllable, reducing overall synthesis complexity while producing compounds with unique odour profiles and superior stability

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP4136067B1Odorants and compositions comprising odorants
Publication Date: 2026.04.15 S H KELKAR & CO LTD
  • EP4136067B1 patent drawing
  • EP4136067B1 patent drawing
  • EP4136067B1 patent drawing

AI summary

The present invention relates to new classes of odorous 3-(2- methylenealkoxy)alkanenitrile derivatives of formula (I) which are useful as fragrance or flavor materials in particular in providing dry, woody, dusty, earthy, and/or patchouli notes together with optional coriander, aldehydic, citrus, mandarin, pear, cinnamon, and/ or petal floral-like notes to perfume, aroma or deodorizing/masking compositions.