Oleocanthal Isolation via Water-Based Self-Emulsifying Extraction

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Solution Overview

Problem

Current methods for isolating oleocanthal from extra-virgin olive oil are inefficient, costly, and environmentally unfriendly, with low yields and significant losses due to the use of organic solvents, making large-scale production and clinical validation challenging.

Innovation Solution

Development of novel extraction methods using ultra-freezing with acetonitrile followed by liquid-liquid extraction and a water-based self-emulsifying method, which reduces solvent consumption and enables high-yield, cost-effective, and environmentally friendly isolation of oleocanthal, allowing for its use in therapeutic applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If traditional organic solvent extraction methods are used to isolate oleocanthal, then extraction efficiency is improved, but solvent consumption increases and environmental friendliness deteriorates

Engineering Contradiction:
Improveextraction efficiencyVSAvoidsolvent consumption
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the extraction parameter from organic solvents to water, transforming the extraction system from oil-soluble to water-soluble based. This parameter change enables extraction without harmful organic solvents while maintaining effectiveness through the formation of water-soluble oleocanthal complexes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces water as an intermediary substance that mediates the extraction of oleocanthal from olive oil. Water acts as a bridge, forming soluble complexes with oleocanthal that enable its separation from the oil phase without requiring traditional organic solvents

Inventive Principle:
Principle #24Intermediary (Mediator)

2Quantity of substance

If traditional extraction methods are used, then oleocanthal can be isolated, but yield is reduced due to cyclic acetal formation and OC loss

Engineering Contradiction:
Improveoleocanthal recoveryVSAvoidoleocanthal loss
Core Design Contradiction:
Quantity of substanceVSLoss of substance

Solution Approach 1:

The patent converts the traditionally harmful effect of water (which causes cyclic acetal formation and oleocanthal loss) into a beneficial extraction medium. By using water as the extraction solvent, the method that previously caused degradation is transformed into the solution, leveraging water's ability to form soluble complexes for effective separation

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Quantity of substance

If current isolation techniques are applied, then oleocanthal can be obtained, but process time increases and cost effectiveness decreases

Engineering Contradiction:
Improveoleocanthal isolationVSAvoidprocess time
Core Design Contradiction:
Quantity of substanceVSLoss of time

Solution Approach 1:

The patent employs a self-service mechanism where water automatically forms soluble complexes with oleocanthal during extraction, enabling spontaneous separation from the oil phase. This self-organizing behavior eliminates the need for complex multi-step purification procedures, significantly reducing process time and operational complexity

Inventive Principle:
Principle #25Self-service

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 new methods significantly improve oleocanthal yield and purity, enabling its potential as a dietary supplement for cancer prevention and treatment, with oral bioavailability and stability, and demonstrate potent in vivo activity against breast cancer recurrence.

Implementation Method 1

liquid-liquid extraction of EVOO with a single organic solvent

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

Implementation Method 2

simple ultra-freezing technique followed by liquid-liquid extraction

Methodology Applied
Scientific EffectFreezing: Freezing

Implementation Method 3

water-based self-emulsifying method

Methodology Applied
Scientific EffectSelf-emulsifying: Emulsion

Data Source

PatentEP3487585B1Oleocanthal isolation
Publication Date: 2023.07.12 BOARD OF SUPERVISORS FOR THE UNIV OF LOUISIANA SYST
  • EP3487585B1 patent drawingFigure 1
  • EP3487585B1 patent drawingFigure 2
  • EP3487585B1 patent drawingFigure 3

AI summary

A method for extracting S (-)-Oleocanthal from olive oil comprising mixing a first volume of water with a second volume of olive oil to form an olive oil/water mixture; letting the olive oil/water mixture stand; removing an aqueous fraction from the olive oil/water mixture leaving a reduced S (-)-Oleocanthal containing olive oil; and filtering the aqueous fraction to create aqueous S (-)-Oleocanthal.