Fisetin Production via Recrystallization and Oxidation

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Solution Overview

Problem

Current methods for producing fisetin are not suitable for mass production due to the limited availability of fisetin from natural sources and the high cost and low yield associated with conventional synthesis methods that require expensive starting materials and time-consuming column chromatography.

Innovation Solution

A method involving the production of a first mixture containing 1-(2-hydroxy-4-methoxy-phenyl)-ethanone and 1-(2,4-dimethoxy-phenyl)-ethanone, followed by reaction with a benzaldehyde compound to form a chalcone compound, and then oxidation with hydrogen peroxide to produce fisetin derivatives, utilizing recrystallization instead of column chromatography for purification.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional synthesis methods using paeonol or quercetin as starting materials are employed, then fisetin can be synthesized, but the process requires expensive starting materials and column chromatography separation, resulting in high cost and reduced product yield

Engineering Contradiction:
Improveproduct purityVSAvoidproduct yield
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent changes the chemical parameters by using different starting materials (phloroglucinol and acetone instead of paeonol or quercetin) and modifies the reaction conditions to eliminate the need for column chromatography. The oxidation step using sodium periodate under controlled conditions directly produces high-purity fisetin, resolving the contradiction between purity and yield.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts or removes the problematic column chromatography separation step from the synthesis pathway. By designing a reaction sequence that produces fisetin directly in high purity through oxidation of the intermediate compound, the method eliminates the need for expensive and time-consuming chromatographic separation, thereby improving both yield and cost-effectiveness.

Inventive Principle:
Principle #2Taking out (Extraction)

2Manufacturing precision

If conventional synthesis methods are used, then fisetin can be produced, but the process requires time-consuming column chromatography for separation, making it unsuitable for mass production

Engineering Contradiction:
Improveproduct purityVSAvoidproduction time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The patent removes the time-consuming column chromatography step from the synthesis pathway by designing a reaction sequence that inherently produces high-purity fisetin. The oxidation step using sodium periodate selectively converts the intermediate to fisetin with high purity, eliminating the need for prolonged separation processes and enabling faster production.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent establishes a continuous synthesis pathway where phloroglucinol reacts with acetone to form an intermediate, which is then directly oxidized to fisetin in sequence without interruption. This continuous process eliminates the downtime associated with column chromatography and enables sustained high-rate production suitable for mass manufacturing.

Inventive Principle:
Principle #20Continuity of useful action

3Manufacturing precision

If conventional synthesis methods are employed, then fisetin can be synthesized, but the process requires expensive starting materials and compound separation, making it economically unviable for mass production

Engineering Contradiction:
Improveproduct purityVSAvoidmanufacturing cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent replaces expensive starting materials (paeonol or quercetin) with inexpensive, readily available chemicals such as phloroglucinol and acetone. These cheap starting materials undergo straightforward reactions to produce fisetin, dramatically reducing the cost of goods while maintaining high product purity through the designed oxidation step.

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

Solution Approach 2:

The patent changes the economic parameters by selecting different starting materials with lower cost and simplifying the purification requirements. The use of phloroglucinol and acetone as starting materials, combined with the selective oxidation step, transforms an expensive, complex synthesis into an economical process suitable for mass production while preserving product purity.

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

This method enables the high-yield production of fisetin derivatives with high purity without the need for intermediate purification, making it more suitable for mass production and reducing costs.

Implementation Method 1

producing fisetin derivatives represented by the following Formula 3 by adding hydrogen peroxide to the second mixture

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11591305B2Method for producing fisetin or fisetin derivatives
Publication Date: 2023.02.28 CATHOLIC UNIV OF DAEGU IND ACADEMIC COOPERATION FOUND
  • US11591305B2 patent drawing
  • US11591305B2 patent drawing
  • US11591305B2 patent drawing

AI summary

The present invention provides a method for producing fisetin or fisetin derivatives, which is capable of mass production. The method for producing fisetin or fisetin derivatives according to the present invention is capable of mass-producing fisetin or fisetin derivatives without a purification process such as a column chromatography process.