Alpha-branched Acyl Carnitine Derivatives for Hydrolysis Resistance

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Solution Overview

Problem

Existing external skin preparations containing carnitine derivatives for stimulating lipid metabolism suffer from poor storage stability and short product life due to the hydrolysis of straight-chain acyl groups in water-based cosmetics, leading to inadequate skin affinity and percutaneous absorption.

Innovation Solution

Development of α-branched acyl carnitine derivatives such as L-carnitine 2-hexyldecanoate, L-carnitine 2-methylpalmitate, and L-carnitine 2-butyloctanoate, which are resistant to hydrolysis in aqueous media, enhancing stability and absorption properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If straight-chain acyl carnitine derivatives are used to stimulate lipid metabolism, then skin penetration and lipid metabolism stimulation effects are improved, but storage stability deteriorates due to hydrolysis in water-based products

Engineering Contradiction:
Improveskin penetration and lipid metabolism stimulation effectsVSAvoidstorage stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical structure parameter of the acyl group from straight-chain to α-branched configuration. This structural modification fundamentally alters the hydrolysis resistance property, allowing the carnitine derivative to maintain stability in water-based cosmetic formulations while retaining skin penetration capabilities and lipid metabolism stimulation effects.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure by combining L-carnitine with α-branched acyl groups (such as 2-hexyldecanoate, 2-methylpalmitate, or 2-butyloctanoate). This composite structure integrates the beneficial properties of both components: the skin-penetrating and metabolically active carnitine core with the hydrolysis-resistant α-branched acyl side chain.

Inventive Principle:
Principle #40Composite materials

2Reliability

If L-carnitine and its salts are used in external skin preparations, then lipid metabolism stimulation is achieved, but percutaneous absorption properties deteriorate due to poor skin affinity

Engineering Contradiction:
Improvelipid metabolism stimulationVSAvoidpercutaneous absorption properties
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent modifies the physical-chemical parameters of carnitine by attaching α-branched acyl groups, which changes the molecular size, lipophilicity, and skin affinity characteristics. This parameter change enables better penetration through the skin barrier while maintaining the ability to stimulate lipid metabolism in target tissues.

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

The novel carnitine derivatives provide superior storage stability and sustained lipid metabolism stimulation, ensuring effective skin penetration and prolonged activity in cosmetic formulations.

Implementation Method 1

α-branched acyl carnitine derivatives, particularly L-carnitine 2-hexyldecanoate, L-carnitine 2-methylpalmitate and L-carnitine 2-butyloctanoate, have superior stability in the presence of aqueous media

Methodology Applied
Scientific EffectHydrolysis resistance: Hydrolysis

Implementation Method 2

the straight-chain acyl carnitine penetrates the skin and produces excellent effects of stimulating the lipid metabolism

Methodology Applied
Scientific EffectPercutaneous absorption: Permeation

Data Source

PatentEP1928402B1Carnitine derivative, salt thereof, external skin preparation and cosmetic preparation
Publication Date: 2014.03.12 RESONAC HOLDINGS CORP
  • EP1928402B1 patent drawingFigure 1
  • EP1928402B1 patent drawingFigure 2
  • EP1928402B1 patent drawing

AI summary

To provide novel carnitine derivatives and salts thereof that are resistant to hydrolysis in the presence of aqueous media, and also provide external skin preparations and cosmetics that are excellent in storage stability, product life, skin affinity and percutaneous absorption properties. In particular, to provide novel a-branched acyl carnitine derivatives and salts thereof, external skin preparations and cosmetics comprising specific a-branched acyl carnitine derivatives and/or salts thereof.