Substituted 3-decene-5-one Derivatives for Green Fruity Fragrance

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Solution Overview

Problem

The fragrance industry faces a continuous need for new chemical entities to create novel perfumes and personal care products, as variations in chemical structure significantly impact odor and characteristics, necessitating the discovery of new compounds to enhance fragrance development.

Innovation Solution

The development of novel chemical compounds represented by Formulas I and II, which include hydrocarbon, cyclic, and aromatic moieties, providing green and fruity notes suitable for use in perfumes, colognes, and personal care products, prepared through specific synthesis methods like the Oppenauer oxidation reaction and nucleophilic addition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If new chemical compounds are developed to create novel fragrance profiles, then fragrance variety and novelty are improved, but research and development time and cost increase

Engineering Contradiction:
Improvefragrance varietyVSAvoiddevelopment time
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The patent applies preliminary action by conducting systematic synthesis of multiple related compounds (Formulas I and II with various R groups) in advance, creating a library of fragrance compounds with different structural variations. This allows perfumers to select from pre-developed options rather than requiring de novo synthesis for each fragrance concept, thereby reducing development time while maintaining fragrance variety.

Inventive Principle:
Principle #10Preliminary action

2Adaptability or versatility

If chemical structure variations are increased to create different odor characteristics, then fragrance characteristics and notes are improved, but synthesis complexity increases

Engineering Contradiction:
Improveodor characteristicsVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the fragrance compound family into two main structural categories (Formula I ketones and Formula II alcohols) with a common core structure, where only specific R groups vary. This modular approach allows independent optimization of different structural elements while maintaining a standardized synthesis platform, reducing overall synthesis complexity despite the variety of odor characteristics achieved.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent applies parameter changes by systematically varying the R group parameter (hydrocarbon chain length, cyclic structures, aromatic groups) while keeping the core molecular framework constant. This allows exploration of different odor characteristics through controlled structural parameter modification rather than complete structural redesign, simplifying the synthesis process while maintaining fragrance diversity.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

These compounds effectively enhance fragrance profiles by offering pleasing green and banana fruity notes, applicable in a wide range of perfumery products, allowing for modification of aroma characteristics and intensity, from 0.005 to 10 weight percent in formulations.

Implementation Method 1

prepared through specific synthesis methods like the Oppenauer oxidation reaction

Methodology Applied
Scientific EffectOppenauer oxidation: Oxidation

Implementation Method 2

prepared through specific synthesis methods like nucleophilic addition

Methodology Applied
Scientific EffectNucleophilic addition: Chemical Bonding

Data Source

PatentUS7491684B2Substituted 3-decene-5-one/ol derivatives
Publication Date: 2009.02.17 INTERNATIONAL FLAVORS & FRAGRANCES INC
  • US7491684B2 patent drawing
  • US7491684B2 patent drawing

AI summary

The present invention is directed to novel ketone and alcohol compounds and the use of these novel compounds in creating fragrances, and scents in items such as perfumes, colognes and personal care products.