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
Engineering 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
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
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
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
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
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
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
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
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
Data Source
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.


