Polymethoxyflavone Purification via Distillation and Adsorption

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Solution Overview

Problem

Current methods for producing polymethoxyflavones from citrus plant peel oil are inefficient, costly, and unsafe for use in food products due to high residual pesticide levels and contamination from other components, limiting their industrial application and safety for human consumption.

Innovation Solution

A method involving the removal of volatile components from citrus peel oil by distillation, followed by thin-film vacuum distillation, extraction with an aqueous ethanol solution, and refinement with active carbon to produce high-purity, stable polymethoxyflavones with reduced pesticide content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional extraction methods using organic solvents are used, then polymethoxyflavones can be extracted from citrus peel oil, but the extract contains contaminants such as hydrocarbon compounds, carbonyl compounds, esters, alcohols, and pigment components that cause altered flavor, off-odor, and coloration

Engineering Contradiction:
Improveextraction efficiencyVSAvoidpurity of polymethoxyflavones
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The extraction process is divided into multiple sequential steps: (1) extraction with organic solvent, (2) filtration to remove insoluble materials, (3) concentration to remove solvent, and (4) purification by silica gel column chromatography. This segmentation allows each step to address specific contaminants systematically, achieving high purity while maintaining extraction efficiency.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Silica gel is introduced as an intermediary substance in the purification step. The silica gel column acts as a mediator that selectively adsorbs polymethoxyflavones from the crude extract, separating them from contaminating components. This intermediary enables high-purity isolation without requiring direct manipulation of the complex mixture.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If column chromatography or high-performance liquid chromatography is used to obtain highly pure polymethoxyflavones, then purity is improved, but large amounts of time and highly expensive organic solvents and special equipment are required, making it impossible to avoid increased costs

Engineering Contradiction:
Improvepurity of polymethoxyflavonesVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention optimizes parameters of the silica gel column chromatography process to improve efficiency: using a specific solvent system (ethyl acetate-hexane or water-acetonitrile), controlling column dimensions and packing density, and optimizing flow rates. These parameter changes maintain high purity while reducing processing time and solvent consumption compared to conventional methods.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The method uses a moderate amount of silica gel (not the excessive amounts required by some conventional protocols) and employs a streamlined column setup that achieves sufficient purification without requiring high-performance liquid chromatography equipment. This partial action approach provides adequate purity for industrial applications while significantly reducing costs and time.

Inventive Principle:
Principle #16Partial or excessive action

3Manufacturing precision

If organic solvents such as n-hexane, ethyl acetate, tetrahydrofuran and acetonitrile are used in column chromatography or high-performance liquid chromatography, then highly pure polymethoxyflavones can be obtained, but these solvents can have adverse effects on the human body, making the use of the obtained polymethoxyflavones in food products inadequate from a safety standpoint

Engineering Contradiction:
Improvepurity of polymethoxyflavonesVSAvoidsafety for food product use
Core Design Contradiction:
Manufacturing precisionVSObject-affected harmful factors

Solution Approach 1:

The invention modifies the solvent system parameters to use safer alternatives: replacing n-hexane with ethyl acetate-hexane mixtures or water-acetonitrile systems, and using ethanol in the final washing step. These parameter changes maintain effective purification while reducing toxicity, making the process suitable for food-grade polymethoxyflavone production.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The method employs readily available, low-cost organic solvents that can be easily removed by evaporation, leaving no harmful residues. The use of common solvents like ethyl acetate, ethanol, and water-acetonitrile mixtures replaces expensive and hazardous solvents, ensuring both economic feasibility and safety for food applications.

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

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 efficient, cost-effective, and safe production of high-purity polymethoxyflavones suitable for use in food products, utilizing previously discarded residues and ensuring stability and safety for industrial-scale application.

Implementation Method 1

a step of removing the volatile components in citrus plant peel oil by distillation to obtain a distillation residue

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

a step of distilling the residue with a thin-film vacuum distillation apparatus to obtain a fraction

Methodology Applied
Scientific EffectVacuum distillation: Vacuum Distillation

Implementation Method 3

a step of extracting the fraction with an aqueous ethanol solution to obtain an extract

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

Implementation Method 4

a step of contacting active carbon with the extract after removal of the insoluble oils in the extract for refining

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentUS8945646B2Method for manufacturing polymethoxyflavones that are highly stable over time and have reduced residual pesticide levels
Publication Date: 2015.02.03 OGAWA & CO LTD
  • US8945646B2 patent drawing
  • US8945646B2 patent drawing
  • US8945646B2 patent drawing

AI summary

There is provided a method for manufacturing inexpensive, highly safe, highly stable, versatile polymethoxyflavones that can be used in food products and easily incorporated into a variety of pharmaceutical formulations, whereby in one pass, a large quantity of polymethoxyflavones can be isolated from other components in citrus peel oil, as well as a method for its use. The method for manufacturing polymethoxyflavones from citrus plant peel oil comprises a step of removing the volatile components in citrus plant peel oil by distillation to obtain a distillation residue, a step of distilling the residue with a thin-film vacuum distillation apparatus to obtain a fraction, a step of extracting the fraction with an aqueous ethanol solution to obtain an extract, and a step of contacting active carbon with the extract after removal of the insoluble oils in the extract for refining, as a method for manufacturing polymethoxyflavones that are highly stable over time and have reduced residual pesticide levels.