Polyphenol Solubility via Cyclodextrin Inclusion Complexes

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Solution Overview

Problem

Polyphenols and flavonoids have limited solubility in water, leading to precipitation in food formulations, which affects product quality and consumer acceptance, and existing solutions either have inadequate taste or limited storage stability.

Innovation Solution

A mixture of polyphenols, flavonoids, or diterpene glucosides combined with polysaccharides and saponins, where the polysaccharides have a high arabinogalactan protein content, allowing for the production of dry powders or granules with improved solubility and taste properties, including enhanced fruit notes and bitterness masking.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If polyphenols and flavonoids are incorporated into food formulations, then health-promoting properties and taste are improved, but solubility decreases and precipitation occurs

Engineering Contradiction:
ImprovestabilityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent uses cyclodextrins as intermediary molecules that form inclusion complexes with polyphenols and flavonoids. The cyclodextrins act as mediators between the hydrophobic active ingredients and the aqueous food matrix, improving solubility and preventing precipitation while maintaining stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention creates composite formulations by combining polyphenols/flavonoids with cyclodextrins and other compatible carriers. This composite approach allows the hydrophobic active ingredients to be dispersed in hydrophilic matrices through the cyclodextrin inclusion complexes, resolving the solubility-stability contradiction.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If spray-drying is used to improve stability, then storage stability increases, but taste quality deteriorates

Engineering Contradiction:
Improvestorage stabilityVSAvoidtaste quality
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the drying parameters and formulation composition to minimize taste deterioration. By optimizing the cyclodextrin-to-active-ingredient ratio and controlling drying conditions, the formulation maintains better taste profiles after spray-drying compared to conventional approaches.

Inventive Principle:
Principle #35Parameter changes

3Object-generated harmful factors

If liquid solubilizing agents are used to improve taste, then mouthfeel improves, but storage stability decreases

Engineering Contradiction:
ImprovemouthfeelVSAvoidstorage stability
Core Design Contradiction:
Object-generated harmful factorsVSStability of the object's composition

Solution Approach 1:

The invention utilizes phase transition from liquid to solid form through spray-drying. The liquid solubilizing system with cyclodextrins provides good mouthfeel, and the phase transition to dried powder form enhances storage stability, allowing the formulation to exhibit both desirable taste properties and improved stability.

Inventive Principle:
Principle #36Phase transitions

4Quantity of substance

If active ingredient content is increased to improve efficacy, then health benefits increase, but solubility and stability worsen

Engineering Contradiction:
Improveactive ingredient contentVSAvoidsolubility
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

Cyclodextrins serve as mediators that enable higher active ingredient loading by forming stable inclusion complexes. This allows increased polyphenol and flavonoid content while maintaining solubility, as the cyclodextrins prevent aggregation and precipitation of the hydrophobic compounds.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 resulting mixtures have a higher active ingredient content, improved solubility, and enhanced taste properties, such as improved mouthfeel and fruitiness, while maintaining stability in dry form, addressing the limitations of previous solutions.

Implementation Method 1

the use of special polysaccharides with a high content of arabinogalactan proteins and preferably also a low ash content allows the production of dry powders or granules, which are initially distinguished from the known liquid preparations by the fact that they have a significantly higher content of polyphenols and flavonoids or diterpene glucosides

Methodology Applied
Scientific EffectSolubilization: Solvation

Implementation Method 2

The mixtures of substances, which are preferably available by spray or freeze-drying appropriate aqueous solutions or dispersions

Methodology Applied
Scientific EffectSpray drying: Evaporation

Implementation Method 3

The Mixtures of substances, which are preferably available by spray or freeze-drying appropriate aqueous solutions or dispersions

Methodology Applied
Scientific EffectFreeze-drying: Freeze Drying

Data Source

PatentEP2628398B1Compositions of matter
Publication Date: 2016.09.07 SYMRISE GMBH & CO KG
  • EP2628398B1 patent drawing
  • EP2628398B1 patent drawing
  • EP2628398B1 patent drawing

AI summary

Proposed are mixtures of substances containing (a) polyphenols, flavonoids and/or diterpene glucosides, (b) polysaccharides and, if applicable, (c) saponins, provided that the content of arabinogalactan proteins in component (b) is at least 11% by weight.