Polymethoxylated Flavonoid Purification via Liquid-Liquid Extraction

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Solution Overview

Problem

There is a need for cost-effective methods to obtain polymethoxylated flavonoids (PMFs) without co-extracting undesirable flavonoids that impart unpleasant tastes to consumers.

Innovation Solution

A process involving the use of an organic oil containing PMFs and hydroxyl-substituted flavonoids, followed by extraction with a water and C1-6 alcohol mixture, separation of phases, and subsequent adsorption chromatography to generate fractions with high PMF concentrations, typically at least 85% by weight.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If extraction methods are used to obtain PMFs from citrus fruits, then PMFs can be obtained, but other flavonoids are co-extracted that impart unpleasant tastes

Engineering Contradiction:
ImprovePMF concentrationVSAvoidunpleasant taste
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent applies extraction by selectively partitioning PMFs into an organic phase using an organic solvent, separating them from hydroxyl-substituted flavonoids that remain in the aqueous phase. This selective extraction removes the harmful co-extracted flavonoids while concentrating the desired PMFs, resolving the contradiction between obtaining sufficient PMF quantity and eliminating unpleasant taste compounds.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent creates different local environments (aqueous phase vs. organic phase) with different solvent properties. By adjusting the local quality of each phase through solvent selection and pH control, PMFs are directed to the organic phase while hydroxyl-substituted flavonoids remain in the aqueous phase, achieving selective separation that resolves the taste quality issue.

Inventive Principle:
Principle #3Local quality

2Manufacturing precision

If pure PMF extraction processes are used, then high purity PMFs are obtained, but the process is cumbersome and costly

Engineering Contradiction:
ImprovePMF purityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent segments the extraction process into distinct phases: aqueous phase containing hydroxyl-substituted flavonoids and organic phase containing PMFs. This segmentation allows for simple phase separation without complex purification equipment, achieving high purity PMFs through a straightforward process that reduces both device complexity and manufacturing cost.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes key parameters including pH level and solvent composition to optimize the separation process. By adjusting these parameters, the process achieves high PMF purity through simple phase separation rather than complex multi-step purification, thereby reducing process complexity and cost while maintaining high manufacturing precision.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If blend extraction of flavonoids is used, then cost effectiveness improves, but unacceptable high concentrations of undesirable flavonoids are present

Engineering Contradiction:
Improvecost effectivenessVSAvoidunpleasant taste
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent introduces an organic solvent as an intermediary that selectively binds to PMFs, forming an organic phase that separates from the aqueous phase containing hydroxyl-substituted flavonoids. This intermediary enables cost-effective extraction of PMFs while the phase separation naturally excludes the undesirable flavonoids, resolving both cost and taste quality issues simultaneously.

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

This process effectively concentrates PMFs to high purity, reducing the concentration of undesirable flavonoids and making PMFs more cost-effective for use in taste modification applications.

Implementation Method 1

introducing an extraction medium to the organic oil to form a mixture having an aqueous phase and an organic phase, wherein the extraction medium comprises water and a C1-6 alcohol

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 2

generating two or more fractions of the separated aqueous phase using adsorption chromatography, wherein at least one of the two or more fractions comprises polymethoxylated flavonoids at a concentration of at least 85% by weight

Methodology Applied
Scientific EffectAdsorption chromatography: Chromatography

Data Source

PatentUS20250145581A1Purification process for polymethoxylated flavonoids and compositions obtained therefrom
Publication Date: 2025.05.08 FIRMENICH SA
  • US20250145581A1 patent drawing
  • US20250145581A1 patent drawing
  • US20250145581A1 patent drawing

AI summary

The present disclosure relates generally to a process for obtaining a naturally derived composition rich in polymethoxylated flavonoids (PMFs). In some embodiments, the process results in a composition in which PMFs make up at least 90% by weight of the flavonoid content in the composition, based on the total weight of flavonoids in the composition. In certain aspects, the disclosure provides compositions resulting from the purification process and the use of such compositions to reduce bitterness, astringency, or sourness, or to enhance 0 sweetness or mouthfeel of an ingestible composition, such as a flavored food or beverage product. In some embodiments, the disclosure provides uses of the resulting composition to reduce the unpleasant taste of limonin, nomilin, or, one or more of which can be present at elevated levels in certain citrus products. naringin