Menthol Glycinate Esters for Prolonged Cooling and Solubility

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Solution Overview

Problem

Existing cooling agents, such as menthol, provide a short-lived cooling sensation and are limited in their ability to enhance flavor and solubility in consumer products.

Innovation Solution

Development of menthol glycinates, which are esters of menthol connected to glycine or glycine derivatives, providing a prolonged cooling effect and improved solubility through a slow hydrolysis rate, allowing for enhanced flavoring in food products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If menthol is used as a cooling agent, then cooling sensation is provided, but the cooling effect is short-lived

Engineering Contradiction:
Improveduration of cooling sensationVSAvoidconsistency of cooling effect
Core Design Contradiction:
Duration of action of moving objectVSReliability

Solution Approach 1:

The patent applies preliminary action by converting menthol into menthol glycinates (esters) beforehand. These esters serve as precursor compounds that slowly hydrolyze to release menthol over time, thereby extending the duration of cooling sensation. The esterification process prepares the menthol in a stable, slow-release form that gradually breaks down to provide sustained cooling effect.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical parameters of menthol by forming esters with glycine or glycine derivatives. This chemical modification alters the hydrolysis rate, solubility, and release profile of menthol, transforming it from a rapidly acting cooling agent into a sustained-release formulation that maintains cooling effect over an extended period.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If menthol is used in consumer products, then cooling sensation is achieved, but solubility and flavor enhancement are limited

Engineering Contradiction:
Improvesolubility of cooling agentVSAvoidflavor enhancement capability
Core Design Contradiction:
Quantity of substanceVSAdaptability or versatility

Solution Approach 1:

The patent modifies the solubility parameters of menthol through esterification with glycine derivatives. The resulting menthol glycinates exhibit improved water solubility compared to native menthol, enabling better incorporation into aqueous-based consumer products while maintaining the characteristic cooling sensation and adding flavor enhancement properties from the glycine component.

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

Menthol glycinates offer a prolonged cooling sensation and improved solubility, making them suitable for various consumer products including toothpaste, mouthwash, candy, gum, and insect repellents, with a slow release of menthol and glycine derivatives.

Implementation Method 1

providing a prolonged cooling effect and improved solubility through a slow hydrolysis rate

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

Menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors is responsible for the well-known cooling sensation it provokes

Methodology Applied
Scientific EffectIon channel activation:

Data Source

PatentUS20260007587A1Derivatives of menthol and uses thereof
Publication Date: 2026.01.08 FONA INTERNATIONAL LLC
  • US20260007587A1 patent drawing
  • US20260007587A1 patent drawing
  • US20260007587A1 patent drawing

AI summary

A compound that includes a menthol glycinate. The menthol glycinate includes a menthol connected to a glycine or glycine derivative, via an ester linkage. The groups on the N atom are referred to as R1 and R2, and R1 and R2 are independently selected from the group consisting of: H, alkyl and R1 and R2 together with the N atom to which they are attached form a 4-8-member ring. R1 and R2 each contain at most 20 carbon atoms.