Ascorbic Acid Derivatives via Epoxide Ring-Opening

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Solution Overview

Problem

Ascorbic acid derivatives and salts used in cosmetics face issues such as coloration, odor generation, and instability over time, which limits their effectiveness and longevity in cosmetic applications, while existing methods for improving stability, like ascorbic acid phosphate and glucoside, are complex and costly.

Innovation Solution

A novel ascorbic acid derivative or salt is developed by reacting ascorbic acid with compounds having an epoxide skeleton, such as glycidol or alkyl glycidyl ether, to create a stable compound with improved whitening, collagen production, and moisturizing effects, which can be produced through a simple and cost-effective method.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If ascorbic acid derivatives are used to improve stability, then stability over time is improved, but coloration and odor generation occur

Engineering Contradiction:
Improvestability over timeVSAvoidcoloration and odor
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of ascorbic acid derivatives by changing the substituent groups (R1-R6) to achieve optimal balance between stability and minimal coloration/odor. This involves systematic variation of chemical parameters such as introducing specific alkyl, alkoxy, or hydroxyl groups at different positions on the molecule to enhance stability while suppressing harmful degradation products

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite ascorbic acid derivative structures combining multiple functional groups (hydroxyl, alkoxy, alkyl) in specific configurations. These composite molecular structures achieve synergistic effects where the combination of different substituents provides both enhanced stability and reduced coloration/odor compared to simpler derivatives

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If ascorbic acid phosphate or glucoside is used to improve stability, then stability over time is improved, but production complexity and cost increase

Engineering Contradiction:
Improvestability over timeVSAvoidproduction complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the complex phosphate and glucoside moieties from ascorbic acid structures, replacing them with simpler alkyl and alkoxy groups. This extraction of unnecessary complex functional groups maintains the desired stability benefit while dramatically simplifying the production process and reducing costs

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent employs simpler, more cost-effective chemical structures that can be produced through straightforward synthesis methods using readily available starting materials. The design prioritizes economical production routes with fewer steps and higher yields, making the derivative accessible for widespread cosmetic application

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Reliability

If ascorbic acid derivatives are used to maintain activity, then whitening and collagen effects are achieved, but endurance of activity in living body is short

Engineering Contradiction:
Improvewhitening and collagen effectsVSAvoidendurance of activity
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent incorporates pre-formed stabilizing functional groups (alkyl and alkoxy substituents) into the ascorbic acid derivative structure before application. These pre-installed protective groups shield the active enediol moiety from premature oxidation and degradation in the living body, extending the duration of biological activity while maintaining effective concentrations of the active form

Inventive Principle:
Principle #10Preliminary action

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 ascorbic acid derivative exhibits excellent stability, minimal coloration and odor change, and sustained activity over time, offering enhanced whitening and collagen production effects, making it suitable for long-term cosmetic use without the complexity and expense of previous solutions.

Implementation Method 1

reacting ascorbic acid with a compound having an epoxide skeleton such as glycidol, alkyl glycidyl ether, epoxy alkane or the like

Methodology Applied
Scientific EffectEpoxide ring-opening reaction: Chemical Bonding

Data Source

PatentEP2189452B1Ascorbic acid derivatives and salts thereof, process for their production, and cosmetic preparations thereof
Publication Date: 2012.11.21 SEIWA KASEI CO JP
  • EP2189452B1 patent drawing
  • EP2189452B1 patent drawing
  • EP2189452B1 patent drawing

AI summary

Disclosed is an ascorbic acid derivative or a salt thereof wherein at least one of hydrogen atoms in hydroxy groups at the 2-position and the 3-position of ascorbic acid is substituted by R-O-CH2-CH(OH)-CH2-, R-O-CH2-CH(CH2OH)-, R-CH(CH2OH)-, R-CH(OH)-CH2- (wherein R represents an alkyl group, an alkenyl group or a phenyl group), or a hydroxycyclohexyl group. Also disclosed is a method for producing an ascorbic acid derivative or a salt thereof, which is characterized by reacting ascorbic acid with an epoxy compound such as an alkyl glycidyl ether, an epoxy alkane or an alicyclic epoxy.