Spiro Compound Receptor Antagonism for Butyric Acid Malodors

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing malodor counteracting (MOC) compositions and ingredients are inadequate in effectively reducing, preventing, or inhibiting the perception of malodors, particularly those containing butyric acid, in environments such as latrines, laundry, and sweat, as they do not sufficiently target specific olfactory receptors.

Innovation Solution

The use of spiro compounds, including (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate and 1,5,10,10-tetramethylspiro[5.5]undec-3-en-11-yl acetate, which act as antagonists to specific olfactory receptors, particularly the butyric acid olfactory receptor, to reduce or inhibit the perception of malodors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If existing malodor counteracting compositions are used, then general malodor suppression is achieved, but specific targeting of olfactory receptors (particularly butyric acid receptors) is insufficient

Engineering Contradiction:
Improvespecificity of olfactory receptor targetingVSAvoideffectiveness in reducing malodor perception
Core Design Contradiction:
Measurement precisionVSReliability

Solution Approach 1:

The patent applies local quality by designing spiro compounds with specific molecular structures (including spiro[4.5]decane and spiro[5.5]undecane skeletons) that are tailored to interact with specific olfactory receptors, particularly butyric acid receptors. This targeted molecular design enables selective binding to specific receptor subtypes rather than general receptor activation, thereby improving both specificity and effectiveness simultaneously.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent utilizes parameter changes by systematically varying molecular parameters such as the spiro ring size (4.5 vs 5.5), substituent positions (2,3,9,9-tetramethyl vs 1,5,10,10-tetramethyl), and functional group modifications to optimize compound affinity for specific olfactory receptors. These parameter variations create a series of compounds with differentiated specificities, allowing selection based on target receptor type.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If spiro compounds with specific structures are used, then binding affinity to olfactory receptors is improved, but synthesis complexity increases

Engineering Contradiction:
Improvebinding affinity to olfactory receptorsVSAvoidsynthesis complexity of spiro compounds
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the spiro compound synthesis into modular steps: first constructing the spiro cyclic skeleton (e.g., spiro[4.5]decane or spiro[5.5]undecane core), then introducing methyl substituents at specific positions, and finally adding functional groups (acetate, formate, or hydroxyl). This stepwise modular approach simplifies the overall synthesis process compared to building complex molecules in a single operation, while maintaining the precise structural requirements for high binding affinity.

Inventive Principle:
Principle #1Segmentation

3Adaptability or versatility

If a broad spectrum malodor counteracting agent is used, then coverage of multiple malodor types is achieved, but effectiveness against specific butyric acid malodors is reduced

Engineering Contradiction:
Improvecoverage of multiple malodor typesVSAvoideffectiveness against butyric acid malodors
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent segments the malodor counteracting strategy into receptor-specific compounds. Instead of using a single broad-spectrum agent, the invention provides distinct spiro compounds tailored for specific receptor families: compounds with spiro[4.5]decane skeletons for certain receptor subtypes and compounds with spiro[5.5]undecane skeletons for other subtypes, including specific butyric acid receptors. This segmentation allows each compound to be optimized for its target receptor, ensuring high effectiveness against butyric acid malodors while maintaining the option to select appropriate compounds for other malodor types.

Inventive Principle:
Principle #1Segmentation

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 spiro compounds effectively inhibit the perception of malodors by targeting specific olfactory receptors, providing a more targeted and effective solution for reducing malodors in environments like latrines, laundry, and sweat.

Implementation Method 1

spiro compounds, including (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate and 1,5,10,10-tetramethylspiro[5.5]undec-3-en-11-yl acetate, which act as antagonists to specific olfactory receptors

Methodology Applied
Scientific EffectReceptor antagonism:

Data Source

PatentEP3713609B1Spiro compounds as malodor counteracting ingredients
Publication Date: 2025.08.06 FIRMENICH SA
  • EP3713609B1 patent drawingFigure 1
  • EP3713609B1 patent drawingFigure 2
  • EP3713609B1 patent drawingFigure 3

AI summary

The various aspects presented herein relate to the perfumery industry. More particularly, the various aspects presented herein relate to malodor counteracting compositions and/or ingredients, methods for counteracting malodors, as well as to the perfumed articles or perfuming compositions comprising as an active ingredient, at least one compound selected from the group consisting of: a compound of Formula (I), a compound of Formula (II), a compound of Formula (III), a compound of Formula (IV), and mixtures thereof.