Anionic Cannabinoid Water Solubility via Deprotonation

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Solution Overview

Problem

Cannabinoids lacking a carboxyl group are insoluble in water, leading to unstable emulsions with undesirable flavor and poor bioavailability, posing challenges for beverage production and consumer confidence.

Innovation Solution

Development of anionic cannabinoid molecules that are water-soluble at mildly-alkaline pH, achieved by deprotonating cannabinoids with a strong Brønsted base and diluting in water with another Brønsted base, allowing for the creation of beverages with enhanced bioavailability and consumer verification through color changes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If cannabinoids are suspended in water to produce beverages, then water-based beverages can be created, but the emulsions display unfavorable characteristics such as undesirable flavor and poor bioavailability

Engineering Contradiction:

Improvebeverage compatibilityVSAvoidbioavailability

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The patent changes the chemical parameter of cannabinoids by converting them to anionic forms through deprotonation with bases like NaOH or KOH. This chemical transformation enables water solubility while maintaining stability and improving bioavailability, resolving the contradiction between beverage compatibility and reliable delivery

Inventive Principle:

Principle #35Parameter changes

2Adaptability or versatility

If cannabinoids are suspended in water through emulsification, then water-based formulations can be produced, but the emulsions display undesirable flavor

Engineering Contradiction:

Improvewater-based formulationVSAvoidflavor quality

Core Design Contradiction:

Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

By changing the chemical state of cannabinoids to anionic forms through deprotonation, the patent achieves true water solubility rather than emulsion. This eliminates the need for emulsifiers and produces clear, stable solutions with improved flavor profiles free from emulsion-related off-tastes

Inventive Principle:

Principle #35Parameter changes

3Reliability

If cannabinoids are made water-soluble through deprotonation, then bioavailability is improved, but the molecules require mildly-alkaline pH conditions

Engineering Contradiction:

ImprovebioavailabilityVSAvoidpH stability range

Core Design Contradiction:

ReliabilityVSTemperature

Solution Approach 1:

The patent applies preliminary deprotonation using strong bases like NaOH or KOH to convert cannabinoids to their anionic forms before beverage formulation. This preliminary chemical action ensures water solubility and stability across the beverage's pH range, allowing the anionic molecules to remain stable even when the final beverage pH varies

Inventive Principle:

Principle #10Preliminary action

Data Source

PatentUS10959961B2Methods of administering anionic cannabinoid molecules dissolved in water

Publication Date: 2021.03.30 NATURAL EXTRACTION SYSTEMS LLC

AI summary

Various aspects of this patent document relate to methods to administer compositions comprising anionic cannabinoid molecules.