Formula I Cooling Compounds for Dual Sensory Effects

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Current chemical compounds with cooling effects, such as carboxamide derivatives, lack additional desirable properties and may not provide simultaneous cooling and sweetening effects effectively in various applications.

Innovation Solution

Development of compounds with the Formula I, where X is S or O, R1 is H or OMe, and R2 is OH, OMe, or OEt, which include 4-(4H-benzo[d][1,3]oxathiin-2-yl)benzonitrile and 4-(4H-benzo[d][1,3]dithiin-2-yl)benzonitrile, offering cooling and sweetening properties when applied to the skin or mucous membranes, and can be used in food, oral care, and cosmetic products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If carboxamide derivatives (WS-3, WS-23) are used for cooling effect, then cooling sensation is provided, but additional desirable properties (sweetening effect) are not achieved

Engineering Contradiction:

Improvefunctional propertiesVSAvoidnumber of compounds

Core Design Contradiction:

Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent combines cooling and sweetening functions into a single chemical compound class (Formula I compounds). The carboxamide group provides cooling sensation while the aromatic substituent (X = S or O, with specific R1, R2, R3 groups) provides sweetening effect, eliminating the need for separate cooling and sweetening agents.

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

The compounds of Formula I are designed to perform multiple functions simultaneously - they act as both cooling agents and sweetening agents. This multi-functionality allows a single compound to replace multiple separate functional ingredients in food, beverage, and oral care products.

Inventive Principle:

Principle #6Universality (Multi-functionality)

2Manufacturing precision

If enantiomers are resolved to obtain pure forms, then optical purity is improved, but manufacturing cost increases

Engineering Contradiction:

Improveoptical purityVSAvoidmanufacturing cost

Core Design Contradiction:

Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent accepts and utilizes racemic mixtures (containing both R and S enantiomers) rather than investing in expensive resolution processes. The racemate form is used directly, significantly reducing manufacturing cost while still providing the desired dual cooling and sweetening effects, as both enantiomers exhibit the required functional properties.

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

3Adaptability or versatility

If single function compounds are used, then functional simplicity is maintained, but application versatility is limited

Engineering Contradiction:

Improveapplication rangeVSAvoidcompound structure

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The compounds of Formula I represent a composite molecular structure combining a carboxamide functional group (for cooling) with specific aromatic substituents (for sweetening). This molecular-level composite structure enables the compound to exhibit multiple functions simultaneously, expanding application versatility while maintaining relatively simple molecular architecture.

Inventive Principle:

Principle #40Composite materials

Data Source

PatentUS8309598B2Cooling compounds

Publication Date: 2012.11.13 GIVAUDAN SA

AI summary

A method of providing a cooling sensation to the skin or the mucous membranes of the body, comprising the application thereto of at least one compound of the Formula Iin which X is selected from S and O, R1 is selected from H and OMe, R2 is selected from OH, OMe and OEt, and R3 is selected from H and OH. Some of the compounds provide simultaneously cooling and sweetening effects.