Violet Leaf Odorants: Chemical Stability and Substantivity

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Solution Overview

Problem

The perfumery industry lacks perfuming ingredients that effectively confer violet leaf odor notes with improved stability and substantivity, as existing compounds either lack organoleptic properties or have different chemical structures that do not provide the desired scent profiles.

Innovation Solution

A compound of formula (I), specifically dec-1-en-4-yne and other stereoisomers, is used as a perfuming ingredient to impart violet leaf and green odor notes, offering stronger and fresher galbanum, truffle, and pear aspects with enhanced stability in perfumery media.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing compounds of formula (I) are used as perfuming ingredients, then they provide violet leaf odor notes, but they lack organoleptic properties and chemical stability

Engineering Contradiction:
Improvechemical stabilityVSAvoidlack of organoleptic properties
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of compounds of formula (I), specifically varying the R1, R2, and R3 substituents to optimize both organoleptic properties and chemical stability. The invention identifies specific compounds where R1 is hydrogen or methyl, R2 is a C3-8 alkyl or unsaturated group, and R3 is hydrogen or methyl, which provide enhanced violet leaf odor notes with improved stability compared to prior art compounds.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If compounds with different chemical structures are used, then they may provide alternative scent profiles, but they do not confer the desired violet leaf odor notes with sufficient stability

Engineering Contradiction:
Improvescent profile varietyVSAvoidsubstantivity
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent applies local quality by focusing on specific structural features within the general formula (I) framework. Rather than exploring entirely different chemical structures, the invention optimizes specific regions of the molecule (the R1, R2, and R3 substituents) to achieve both desired violet leaf odor notes and improved substantivity. This localized optimization allows maintaining the core structural framework while achieving enhanced performance.

Inventive Principle:
Principle #3Local quality

3Object-generated harmful factors

If prior art compounds like 1,3-undecadien-5-yne are used, then they provide floral green galbanum odor, but they lack the strength and freshness of violet leaf notes

Engineering Contradiction:
Improveodor strengthVSAvoidchemical structure similarity
Core Design Contradiction:
Object-generated harmful factorsVSStability of the object's composition

Solution Approach 1:

The patent applies asymmetry by introducing specific structural variations in the compounds of formula (I) that create asymmetric substitution patterns. The combination of R1 (hydrogen or methyl), R2 (C3-8 alkyl or unsaturated group), and R3 (hydrogen or methyl) creates structurally asymmetric compounds that provide stronger and fresher violet leaf odor notes compared to the more symmetric prior art compounds like 1,3-undecadien-5-yne.

Inventive Principle:
Principle #4Asymmetry

Data Source

PatentUS9243210B2Violet leaves odorants
Publication Date: 2016.01.26 FIRMENICH SA
  • US9243210B2 patent drawing
  • US9243210B2 patent drawing
  • US9243210B2 patent drawing

AI summary

A method of use, as a perfuming ingredient, of a compound of formula Iin the form of any one of its stereoisomers or a mixture thereof, and wherein each R1 represents a hydrogen atom or a methyl group and at least one of said R1 is a hydrogen atom; R2 represents a linear or branched C3-8 alkyl group or unsaturated groups; and R3 represents a hydrogen atom or a methyl group. These compounds impart odor notes of the violet leaves type optionally together with green odor notes.