5,9-Dimethyl-9-Hydroxy-Decen-4-Al Synthesis for Stable Fragrance

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Solution Overview

Problem

The existing compound 4(4-hydroxy-4-methylpentyl) 3-cyclohexene carboxaldehyde (cyclohexal) is valued for its muguet odor but faces allergenic concerns and potential regulatory issues, necessitating the development of alternative fragrance ingredients with similar odor characteristics and performance.

Innovation Solution

The compound 5,9-dimethyl-9-hydroxy-decen-4-al is synthesized using a modified process that avoids alkaline and acidic conditions to ensure thermal stability, allowing for the production of a fragrance with a classic floral, green muguet odor, and is used in perfume compositions as a replacement for cyclohexal.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If cyclohexal is used as a fragrance ingredient, then muguet odor characteristics are achieved, but allergenic concerns and regulatory issues arise

Engineering Contradiction:

Improveodor characteristicsVSAvoidallergenic concerns

Core Design Contradiction:

Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent creates a structural analog of cyclohexal (formula I) that copies the essential odor characteristics while eliminating the harmful allergenic properties. The new compound maintains the floral muguet profile through similar molecular features (aldehyde group, carbon chain length) while avoiding the specific structural motif that causes allergies in cyclohexal.

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The invention modifies key molecular parameters of cyclohexal by changing the carbon chain length, introducing different functional groups, and adjusting the overall molecular structure. These parameter changes preserve the odor profile while altering the chemical properties to reduce allergenicity and improve safety.

Inventive Principle:

Principle #35Parameter changes

2Productivity

If conventional synthesis methods are used for gamma,delta-unsaturated aldehydes, then production is achieved, but thermal stability is compromised due to alkaline and acidic conditions

Engineering Contradiction:

ImproveproductionVSAvoidthermal stability

Core Design Contradiction:

ProductivityVSStability of the object's composition

Solution Approach 1:

The patent converts the harmful effect of thermal degradation into a beneficial selective process. By using mild conditions (neutral pH, lower temperatures) that would normally be insufficient for synthesis, the method selectively produces the desired aldehyde without degradation, while harsh conditions would cause decomposition. The mild conditions become the advantage, enabling stable product formation.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The invention changes the reaction parameters from conventional harsh conditions (strong base, high temperature) to mild conditions (neutral or slightly acidic pH, lower temperature). This parameter modification maintains productivity while ensuring thermal stability of the product, as the gentler conditions prevent degradation during synthesis and storage.

Inventive Principle:

Principle #35Parameter changes

3Ease of manufacture

If existing fragrance ingredients are used, then odor performance is achieved, but safety and stability profile are insufficient

Engineering Contradiction:

Improveodor performanceVSAvoidstability and safety profile

Core Design Contradiction:

Ease of manufactureVSReliability

Solution Approach 1:

The patent develops a structural analog that copies the successful odor performance of existing ingredients like cyclohexal while improving the safety and stability profile. The new compound (formula I) replicates the floral character, longevity, and fragrance fixation properties through analogous molecular features, while eliminating the safety concerns associated with conventional ingredients.

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The invention creates a composite fragrance formulation by combining the new compound (formula I) with complementary fragrance ingredients (formula II). This composite approach enhances the overall stability and safety profile while maintaining superior odor performance, as the combination provides synergistic effects that improve both sensory properties and formulation stability.

Inventive Principle:

Principle #40Composite materials

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

The synthesized 5,9-dimethyl-9-hydroxy-decen-4-al effectively replicates the odor characteristics of cyclohexal, offering a suitable replacement with improved stability and safety profile, suitable for use in fine perfumery and personal care products.

Implementation Method 1

The compound according to the present invention was found by the applicant to have a classic floral, green muguet odour note that was reminiscent of cyclohexal

Methodology Applied

Scientific EffectOdor replication through molecular structure:

Data Source

PatentUS10315976B2Organic compounds

Publication Date: 2019.06.11 GIVAUDAN SA

AI summary

5,9-dimethyl-9-hydroxy-decen-4-al, having the formula (I)