Resveratrol 3-O-α-glucoside Solubility and Stability

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Solution Overview

Problem

Current resveratrol derivatives, such as resveratrol 3-O-β-glucoside, have limitations in water solubility and functionality, particularly in pharmaceutical formulations, where they exhibit poor stability and reduced tyrosinase inhibitory effects, making them unsuitable for effective skin aging prevention.

Innovation Solution

Development of resveratrol 3-O-α-glucoside, which is mixed with monohydric to tetrahydric alcohols to enhance solubility and stability, allowing for high concentration concentration and incorporation into various products like cosmetics, foods, and medicines, demonstrating improved melanogenesis suppression, hyaluronidase inhibition, anti-oxidization, cell activation, sirtuin gene activation, and anti-inflammatory properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If resveratrol 3-O-β-glucoside is used to improve water solubility and stability, then stability is improved, but water solubility remains insufficient and tyrosinase inhibitory effect is reduced

Engineering Contradiction:
ImprovestabilityVSAvoidwater solubility
Core Design Contradiction:
Stability of the object's compositionVSQuantity of substance

Solution Approach 1:

The patent changes the glycosidic bond configuration parameter from β to α, transforming resveratrol 3-O-β-glucoside into resveratrol 3-O-α-glucoside. This parameter change fundamentally alters the physical and chemical properties, achieving both high water solubility (approximately 10-fold higher than resveratrol) and enhanced stability, while simultaneously improving tyrosinase inhibitory effect.

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If resveratrol derivatives are used to improve stability, then stability is improved, but water solubility and functionality remain unsatisfactory

Engineering Contradiction:
ImprovestabilityVSAvoidfunctionality
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The patent modifies the glycosidic bond configuration from β to α, which fundamentally changes the molecular structure and physical properties. This parameter change results in resveratrol 3-O-α-glucoside exhibiting high water solubility, enhanced stability, and improved tyrosinase inhibitory effect, thereby resolving the functionality issue.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If conventional resveratrol derivatives are used in pharmaceutical formulations, then stability is improved, but water solubility prevents effective concentration

Engineering Contradiction:
ImprovestabilityVSAvoidwater solubility
Core Design Contradiction:
Stability of the object's compositionVSQuantity of substance

Solution Approach 1:

The patent changes the glycosidic bond configuration parameter from β to α, creating resveratrol 3-O-α-glucoside with fundamentally improved water solubility. This parameter change enables the compound to achieve high concentrations in aqueous pharmaceutical formulations while maintaining stability, overcoming the solubility limitation of conventional derivatives.

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

Resveratrol 3-O-α-glucoside effectively prevents skin aging by suppressing melanogenesis, inhibiting hyaluronidase, reducing oxidative stress, activating skin cells, promoting sirtuin gene expression, and acting as an anti-inflammatory, while maintaining stability and solubility, enabling its use in diverse products for skin health.

Implementation Method 1

resveratrol 3-O-α-glucoside has a melanogenesis suppressing effect

Methodology Applied
Scientific EffectMelanogenesis suppression:

Implementation Method 2

hyaluronidase inhibition

Methodology Applied
Scientific EffectHyaluronidase inhibition:

Implementation Method 3

anti-oxidization

Methodology Applied
Scientific EffectAnti-oxidization: Oxidation

Implementation Method 4

cell activation

Methodology Applied
Scientific EffectCell activation:

Implementation Method 5

sirtuin gene activation

Methodology Applied
Scientific EffectSirtuin gene activation:

Implementation Method 6

matrix metalloproteinase suppression

Methodology Applied
Scientific EffectMatrix metalloproteinase suppression:

Implementation Method 7

anti-inflammation

Methodology Applied
Scientific EffectAnti-inflammation:

Data Source

PatentEP3130331B1Skin aging inhibitor and concentrate of resveratrol 3-o-alpha-glucoside
Publication Date: 2021.05.26 EZAKI GLICO CO LTD
  • EP3130331B1 patent drawingFigure 1
  • EP3130331B1 patent drawing
  • EP3130331B1 patent drawing

AI summary

An object of the present invention is to provide an anti-skin aging agent that can prevent skin aging such as spots, dullness, wrinkles, sags, and skin roughness. It has been found that resveratrol 3-O-α-glucoside has remarkable anti-skin aging effects such as melanogenesis suppression, hyaluronidase inhibition, anti-oxidization, cell activation, sirtuin gene activation, matrix metalloproteinase suppression, and anti-inflammation, and thus, can be used as an anti-skin aging agent.